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Journal articles on the topic 'Tributylstannane'

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Published: 4 June 2021

Last updated: 19 February 2022

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1

Imrich, Michael R., and Thomas Ziegler. "Access to d- and l-Psicose Derivatives via Hydroxy Methylation of Ribono Lactone." Molbank 2019, no. 4 (December 10, 2019): M1096. http://dx.doi.org/10.3390/m1096.

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2,3,5-Tri-O-benzyl- and 2,3,5-tri-O-methyl-d-ribono-γ-lactone were converted with (methoxyethoxymethoxy)methyl and benzyloxy tributylstannane into the corresponding protected d-psicoses as mixtures of anomers in 31%–72% yield. Treatment of 2,3,5-tri-O-methyl-l-ribono-γ-lactone with benzyloxy tributylstannane afforded the corresponding l-psicose derivative as an anomeric mixture in 72% yield. Both methylated psicoses were further converted into 1,2-O-isopropylidene-3,4,6-tri-O-methyl-d- and l-psicofuranosides, the respective α- and β-anomers of which could be separated and characterized.

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2

Samano, Vincente, and Morris J. Robins. "Nucleic acid related compounds. 77. 2′,3′-Didehydro-2′,3′-dideoxy-2′(and 3′)-methylnucleosides via [3,3]-sigmatropic rearrangements of 2′(and 3′)-methylene-3′(and 2′)-O-thiocarbonyl derivatives and radical reduction of a 2′-chloro-3′-methylene analogue." Canadian Journal of Chemistry 71, no. 2 (February 1, 1993): 186–91. http://dx.doi.org/10.1139/v93-027.

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Treatment of 5′-O-(tert-butyldiphenylsilyl)-2′(and 3′)-deoxy-2′(and 3′)-methyleneuridine (and adenosine) derivatives with phenyl chlorothionocarbonate gave the 3′(and 2′)-O-phenoxythiocarbonyl intermediates, which underwent spontaneous [3,3]-sigmatropic rearrangement to give the 2′,3′-didehydro-2′,3′-dideoxy-2′(and 3′)-(phenoxycarbonylthio)methyl analogues. These allylic thioesters were subjected to tributylstannane-mediated hydrodesulfurization and deprotection to give 2′,3′-didehydro-2′,3′-dideoxy-2′(and 3′)-methyluridine (and adenosine). Tributylstannane-mediated hydrodehalogenation of a 2′-chloro-2′,3′-dideoxy-3′-methyleneuridine derivative afforded the 2′,3′-didehydro-2′,3′-dideoxy-3′-methyl product of allylic transposition exclusively.

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3

Leung, Lai To, and Pauline Chiu. "Hydrostannation of activated alkynes mediated by Stryker's reagent." Pure and Applied Chemistry 78, no. 2 (January 1, 2006): 281–85. http://dx.doi.org/10.1351/pac200678020281.

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The treatment of activated alkynes with catalytic amounts of Stryker's reagent and tributylstannane resulted in hydrostannation. The reaction proceeds with high regioselectivity to produce α-stannated vinylstannanes exclusively.

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4

Bachi, Mario D., Eric Bosch, Daniella Denenmark, and Diana Girsh. "Tributylstannane-mediated cyclization of thionocarboxylic acid derivatives." Journal of Organic Chemistry 57, no. 25 (December 1992): 6803–10. http://dx.doi.org/10.1021/jo00051a024.

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5

Masiuk, Uladzimir S., Iryna V. Mineyeva, and Dzmitry G. Kananovich. "Highly Diastereoselective Chelation-Controlled 1,3-anti-Allylation of (S)-3-(Methoxymethyl)hexanal Enabled by Hydrate of Scandium Triflate." Symmetry 13, no. 3 (March 13, 2021): 470. http://dx.doi.org/10.3390/sym13030470.

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En route to the total synthesis of (+)-Neopeltolide, we explored Lewis acid-assisted diastereoselective allylation of MOM-protected 3-hydroxylhexanal with β-(2,2-diethoxyethyl)-substituted (allyl)tributylstannane. The hydrated form of scandium triflate was found to be essential for attaining high 1,3-anti-diastereoselectivity (d.r. 94:6), while the use of anhydrous catalyst resulted in a modest diastereocontrol (d.r. 76:24). The preferred 1,3-anti-selectivity in this transformation can be rationalized in the framework of the Reetz chelate model of asymmetric induction. The 1,3-anti-configuration of the product was confirmed by its conversion into the known C7-C16 building block of (+)-Neopeltolide. We also report an improved protocol for the synthesis of β-(2,2-diethoxyethyl)-substituted (allyl)tributylstannane, which can be utilized as a cost-efficient bipolar isoprenoid-type C5-building block in the synthesis of natural compounds.

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6

BACHI, M. D., E. BOSCH, D. DENENMARK, and D. GIRSH. "ChemInform Abstract: Tributylstannane-Mediated Cyclization of Thionocarboxylic Acid Derivatives." ChemInform 24, no. 18 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199318108.

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7

Liu, Qibo, and Donald J. Burton. "Preparation of E-(1,2-difluoro-1,2-ethenediyl)bis(tributylstannane)." Journal of Fluorine Chemistry 131, no. 11 (November 2010): 1082–85. http://dx.doi.org/10.1016/j.jfluchem.2009.12.025.

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8

Bachi, Mario D., and Eric Bosch. "On the mechanism of reductive degradation of dithiocarbonates by tributylstannane." Journal of the Chemical Society, Perkin Transactions 1, no. 6 (1988): 1517. http://dx.doi.org/10.1039/p19880001517.

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9

Barton, Derek H. R., David Crich, Antonius Löbberding, and Samir Z. Zard. "On the mechanism of reduction of dithiocarbonates (xanthates) with tributylstannane." J. Chem. Soc., Chem. Commun., no. 10 (1985): 646–47. http://dx.doi.org/10.1039/c39850000646.

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10

Johnson, Carl R., and John R. Medich. "Efficient preparation of [(methoxymethoxy)methyl]tributylstannane, a convenient hydroxymethyl anion equivalent." Journal of Organic Chemistry 53, no. 17 (August 1988): 4131–33. http://dx.doi.org/10.1021/jo00252a054.

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11

Tsuji, Yasushi, Satoshi Kajita, Shinya Isobe, and Masahiro Funato. "Palladium-catalyzed silylation of allylic acetates with hexamethyldisilane or (trimethylsilyl)tributylstannane." Journal of Organic Chemistry 58, no. 14 (July 1993): 3607–8. http://dx.doi.org/10.1021/jo00066a005.

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12

Liu, Qibo, and Donald J. Burton. "ChemInform Abstract: Preparation of E-(1,2-Difluoro-1,2-ethenediyl)bis(tributylstannane)." ChemInform 42, no. 12 (February 24, 2011): no. http://dx.doi.org/10.1002/chin.201112187.

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13

Buffet, Marianne F., Darren J. Dixon, Steven V. Ley, and Edward W. Tate. "Anomeric Oxygen to Carbon Rearrangements of Alkynyl Tributylstannane Derivatives of Lactols." Synlett 1998, no. 10 (October 1998): 1091–92. http://dx.doi.org/10.1055/s-1998-1866.

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14

Franz, James A., Naushadali K. Suleman, and Mikhail S. Alnajjar. "Absolute rate constants for hydrogen atom abstraction by benzyl radical from thiophenol, tributylstannane, tributylstannane-d, and dicyclohexylphosphine and for the cyclization of the 2-allylbenzyl radical." Journal of Organic Chemistry 51, no. 1 (January 1986): 19–25. http://dx.doi.org/10.1021/jo00351a004.

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15

Robins, Morris J., Danuta Madej, Fritz Hansske, John S. Wilson, Gilles Gosselin, Marie-Christine Bergogne, Jean-Louis Imbach, Jan Balzarini, and Erik De Clercq. "Nucleic acid related compounds. 53. Synthesis and biological evaluation of 2′-deoxy-β-threo-pentofuranosyl nucleosides. "Reversion to starting alcohol" in Barton-type reductions of thionocarbonates." Canadian Journal of Chemistry 66, no. 5 (May 1, 1988): 1258–62. http://dx.doi.org/10.1139/v88-204.

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Treatment of selectively 3′,5′-protected β-D-xylofuranosyl nucleosides (4) with phenyl chlorothionocarbonate and DMAP followed by hydrogenolysis of the resulting (2′-O-phenoxythiocarbonyl) phenyl thionocarbonate esters (6) with tributylstannane/AIBN, and deprotection, gave 2′-deoxy-β-D-threo-pentofuranosyl nucleosides (7). Formation of a by-product bis(nucleosid-2′-yl)thionocarbonate dimer (8) was detected in the uracil nucleoside reaction sequence. Its subsequent reduction provides one explanation for "reversion to starting alcohol" in Barton-type deoxygenation reactions. Only the guanine 2′-deoxynucleoside analogue (7b) had (weak) antiviral activity (against herpes simplex virus type 1).

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16

Brody, Marcus S., and M. G. Finn. "Palladium-catalyzed coupling of functionalized bromoarenes to a polystyrene-bound aryl tributylstannane." Tetrahedron Letters 40, no. 3 (January 1999): 415–18. http://dx.doi.org/10.1016/s0040-4039(98)02384-3.

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17

Kvíčala, Jaroslav, Tomáš Bříza, Oldřich Paleta, and Jan Čermák. "Synthesis of (Polyfluoroalkyl)cyclopentenes as Model Compounds for Fluorophilic Cyclopentadienes." Collection of Czechoslovak Chemical Communications 67, no. 9 (2002): 1345–58. http://dx.doi.org/10.1135/cccc20021345.

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Nucleophilic opening of the epoxide ring in 6-oxabicyclo[3.1.0]hexane (1) with ethenylmagnesium bromide was employed for the preparation of 2-ethenylcyclopentan-1-ol (2). Radical addition of perfluoroalkyl iodides 3 to alcohol 2 afforded (polyfluoroiodoalkyl)cyclopentanols 4, which were deiodinated with tributylstannane to (polyfluoroalkyl)cyclopentanols 5, followed by dehydration with Nafion-H to the target (polyfluoroalkyl)cyclopentenes 6, which are potential intermediates for fluorous chemistry. Attempts to synthesize (polyfluoroalkyl)cyclopentadienes or bis(polyfluoroalkyl)cyclopentadienes failed due to the exclusive formation of unexpected side product, polyfluoroiodoalkanol 7, in the course of radical addition of perfluoroalkyl iodides 3 to ethenylcyclopentenol (8) or diethenylcyclopentanediol (9), respectively.

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18

Tresse, Cédric, Stéphane Schweizer, Philippe Bisseret, Jacques Lalevée, Gwilherm Evano, and Nicolas Blanchard. "Stereodivergent Hydrosilylation, Hydrostannylation, and Hydrogermylation of α-Trifluoromethylated Alkynes and Their Synthetic Applications." Synthesis 48, no. 19 (July 22, 2016): 3317–30. http://dx.doi.org/10.1055/s-0035-1561487.

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Stereoselective hydrometalation reactions of aryl- and alkyl-substituted trifluoromethylated alkynes with triethylsilane, tributylstannane, and triphenylgermane have been investigated. (E)-α-CF3-Vinylsilanes, -stannanes, and -germanes were obtained under palladium-catalyzed conditions whereas the corresponding (Z)-α-CF3-vinylgermanes were obtained under radical conditions. These reactions proceed in good to excellent yields and possess a broad functional group tolerance. Applications of the (Z)- and (E)-α-CF3-vinylgermanes in palladium-catalyzed cross-coupling reactions with aryl halides having diverse electronic requirements were also investigated. The corresponding (Z)- and (E)-α-CF3-styrenes were obtained as single isomers, thus demonstrating the utility of these versatile synthons for the synthesis of stereodefined trifluoromethylated alkenes.

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19

TSUJI, Y., S. KAJITA, S. ISOBE, and M. FUNATO. "ChemInform Abstract: Palladium-Catalyzed Silylation of Allylic Acetates with Hexamethyldisilane or (Trimethylsilyl)tributylstannane." ChemInform 24, no. 42 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199342217.

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20

BUFFET, M. F., D. J. DIXON, S. V. LEY, and E. W. TATE. "ChemInform Abstract: Anomeric Oxygen to Carbon Rearrangements of Alkynyl Tributylstannane Derivatives of Lactols." ChemInform 30, no. 4 (June 17, 2010): no. http://dx.doi.org/10.1002/chin.199904136.

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21

Masyuk, V. S., and I. V. Mineeva. "Synthesis of β-(2,2-diethoxyethyl)-substituted (allyl)tributylstannane and its application to asymmetric allylation." Russian Journal of Organic Chemistry 52, no. 2 (February 2016): 178–85. http://dx.doi.org/10.1134/s1070428016020020.

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22

Horton, Derek, Waldemar Priebe, and Marcos L. Sznaidman. "Steric and conformational effects in the dehalogenation of 2-halo sugar derivatives with tributylstannane." Journal of Organic Chemistry 58, no. 7 (March 1993): 1821–26. http://dx.doi.org/10.1021/jo00059a037.

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23

Egger, Anita, J�rg Hunziker, Christian Leumann, and Grethy Rihs. "Synthesis of Bridgehead-Functionalized Bicyclo[3.2.1]octanesvia intramolecular titanium- and tributylstannane-induced pinacol coupling." Helvetica Chimica Acta 81, no. 3-4 (1998): 734–43. http://dx.doi.org/10.1002/hlca.19980810323.

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24

Khan, Faiz Ahmed, and B. Prabhudas. "A simple and preparatively useful tributylstannane mediated selective reduction and bridgehead functionalization of tetrahalonorbornene derivatives." Tetrahedron Letters 40, no. 52 (December 1999): 9289–92. http://dx.doi.org/10.1016/s0040-4039(99)01948-6.

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25

Lautens, Mark, Nicholas D. Smith, and Dennis Ostrovsky. "Palladium-Catalyzed Hydrostannation−Cyclization of 1,6-Diynes. Generation of 1,2-Dialkylidenecyclopentanes with a Tributylstannane Moiety." Journal of Organic Chemistry 62, no. 26 (December 1997): 8970–71. http://dx.doi.org/10.1021/jo971788f.

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26

Fischer, Jason M., Warren E. Piers, Susan D. Pearce Batchilder, and Michael J. Zaworotko. "Titanium-Mediated Heterodehydrocoupling of Tributylstannane and Tellurium. X-ray Structure of (C5Me5)2TiTeSn(C6H5)3." Journal of the American Chemical Society 118, no. 1 (January 1996): 283–84. http://dx.doi.org/10.1021/ja953081l.

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27

Hřebabecký, Hubert, and Antonín Holý. "Synthesis of 1-(2,3-Dideoxy-4-C-methyl-β-D-glycero-pent-2-enofuranosyl)thymine, 1-(2,3-Dideoxy-4-C-methyl-β-D-glycero-pentofuranosyl)thymine and 1-(4-C-Azidomethyl-2-deoxy-β-D-threo-pentofuranosyl)thymine." Collection of Czechoslovak Chemical Communications 58, no. 7 (1993): 1668–74. http://dx.doi.org/10.1135/cccc19931668.

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Reaction of isopropylidene derivative I with thionyl chloride in hexamethylphosphoric triamide afforded chloro derivative II. Removal of the isopropylidene group in II by treatment with a cation-exchanging resin (H+ form) gave the free chloro nucleoside III. reduction of the chloro derivative II with tributylstannane and subsequent removal of the isopropylidene group yielded deoxy derivative V. This was protected with tert-butyldiphenylsilyl group and converted into the mesylate VII. Elimination of the mesyl group followed by desilylation gave 1-(2,3-dideoxy-4-C-methyl-β-D-glycero-pent-2-enofuranosyl)thymine (IX) which was hydrogenated to afford 1-(2,3-dideoxy-4-C-methyl-β-D-glycero-pentofuranosyl)thymine (X). 1-(1-C-Azidomethyl-2-deoxy-β-D-threo-pentofuranosyl)thymine (XIII) was prepared by mesylation of the isopropylidene derivative I, nucleophilic substitution of the mesyl group with azide and removal of the isopropylidene group.

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28

Han, Seung Yeon, Hyo Young Lee, Jong Hee Jeon, and In Howa Jeong. "Preparation of (2,2-difluoroethenylidene)bis(tributylstannane) and arylation reaction: efficient approach to 1,1-diaryl-2,2-difluoroethenes." Tetrahedron Letters 53, no. 14 (April 2012): 1833–36. http://dx.doi.org/10.1016/j.tetlet.2012.01.127.

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29

Buffet, Marianne F., Darren J. Dixon, Steven V. Ley, Dominic J. Reynolds, and R. Ian Storer. "Anomeric oxygen to carbon rearrangements of alkynyl tributylstannane derivatives of furanyl (γ)- and pyranyl (δ)-lactols." Org. Biomol. Chem. 2, no. 8 (2004): 1145–54. http://dx.doi.org/10.1039/b316858a.

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30

Samano, Mirna C., and Morris J. Robins. "Efficient reduction of azides to amines with tributylstannane. high-yield syntheses of amino and diamino deoxynucleosides." Tetrahedron Letters 32, no. 44 (October 1991): 6293–96. http://dx.doi.org/10.1016/0040-4039(91)80150-5.

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31

Ishizaki, Miyuki, and Osamu Hoshino. "Unprecedented Cesium and Potassium Fluorides Catalyzed Trialkylsilylation and Tributylstannylation of Terminal Alkynes with Trifluoromethyl-Trialkylsilanes and -Tributylstannane." Tetrahedron 56, no. 45 (November 2000): 8813–19. http://dx.doi.org/10.1016/s0040-4020(00)00810-3.

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32

LAUTENS, M., N. D. SMITH, and D. OSTROVSKY. "ChemInform Abstract: Palladium-Catalyzed Hydrostannation-Cyclization of 1,6-Diynes. Generation of 1,2-Dialkylidenecyclopentanes with a Tributylstannane Moiety." ChemInform 29, no. 19 (June 22, 2010): no. http://dx.doi.org/10.1002/chin.199819181.

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33

EGGER, A., J. HUNZIKER, G. RIHS, and C. LEUMANN. "ChemInform Abstract: Synthesis of Bridgehead-Functionalized Bicyclo[3.2.1]octanes via Intramolecular Titanium- and Tributylstannane-Induced Pinacol Coupling." ChemInform 29, no. 29 (June 20, 2010): no. http://dx.doi.org/10.1002/chin.199829260.

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34

Khan, Faiz Ahmed, and B. Prabhudas. "ChemInform Abstract: A Simple and Preparatively Useful Tributylstannane-Mediated Selective Reduction and Bridgehead Functionalization of Tetrahalonorbornene Derivatives." ChemInform 31, no. 14 (June 9, 2010): no. http://dx.doi.org/10.1002/chin.200014077.

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35

Liu, Qibo, and Donald J. Burton. "Stereoselective Preparation of (E)-(1,2-Difluoro-1,2-ethenediyl) Bis[tributylstannane] and Stereospecific Synthesis of (E)-1,2-Difluorostilbenes." Organic Letters 4, no. 9 (May 2002): 1483–85. http://dx.doi.org/10.1021/ol025686+.

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36

Wnuk, Stanislaw F., Mukesh M. Mudgal, Ireneusz Nowak, and Morris J. Robins. "Model Substrate/Inactivation Reactions for MoaA and Ribonucleotide Reductases: Loss of Bromo, Chloro, or Tosylate Groups from C2 of 1,5-Dideoxyhomoribofuranoses upon Generation of an α-Oxy Radical at C3." Molecules 25, no. 11 (May 29, 2020): 2539. http://dx.doi.org/10.3390/molecules25112539.

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We report studies on radical-initiated fragmentations of model 1,5-dideoxyhomoribofuranose derivatives with bromo, chloro, and tosyloxy substituents on C2. The effects of stereochemical inversion at C2 were probed with the corresponding arabino epimers. In all cases, the elimination of bromide, chloride, and tosylate anions occurred when the 3-hydroxyl group was unprotected. The isolation of deuterium-labeled furanone products established heterolytic cleavage followed by the transfer of deuterium from labeled tributylstannane. In contrast, 3-O-methyl derivatives underwent the elimination of bromine or chlorine radicals to give the 2,3-alkene with no incorporation of label in the methyl vinyl ether. More drastic fragmentation occurred with both of the 3-O-methyl-2-tosyloxy epimers to give an aromatized furan derivative with no deuterium label. Contrasting results observed with the present anhydroalditol models relative to our prior studies with analogously substituted nucleoside models have demonstrated that insights from biomimetic chemical reactions can provide illumination of mechanistic pathways employed by ribonucleotide reductases (RNRs) and the MoaA enzyme involved in the biosynthesis of molybdopterin.

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37

Hanckel, John M., Kang Wook Lee, Paul Rushman, and Theodore L. Brown. "Steric and electronic effects on atom transfer reactions of Re(CO)4L.cntdot. radicals with organic halides and tributylstannane." Inorganic Chemistry 25, no. 11 (May 1986): 1852–56. http://dx.doi.org/10.1021/ic00231a027.

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38

Mori, Miwako, Naohiro Isono, Naotake Kaneta, and Masakatsu Shibasaki. "Novel cyclization by stannyl anion generated from (trimethylsilyl)tributylstannane (Me3SiSnBu3) and fluoride ion. Application to natural product synthesis." Journal of Organic Chemistry 58, no. 11 (May 1993): 2972–76. http://dx.doi.org/10.1021/jo00063a012.

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39

Han, Seung Yeon, Hyo Young Lee, Jong Hee Jeon, and In Howa Jeong. "ChemInform Abstract: Preparation of (2,2-Difluoroethenylidene)bis(tributylstannane) and Arylation Reaction: Efficient Approach to 1,1-Diaryl-2,2-difluoroethenes." ChemInform 43, no. 29 (June 21, 2012): no. http://dx.doi.org/10.1002/chin.201229063.

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40

Kuniyasu, Hitoshi, Akiya Ogawa, Keigo Higaki, and Noboru Sonoda. "Palladium-catalyzed chemo- and site-selective reduction of (Z)-1,3-bis(arylseleno)-2-alken-1-ones with tributylstannane." Organometallics 11, no. 12 (December 1992): 3937–39. http://dx.doi.org/10.1021/om00060a005.

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41

Krečmerová, Marcela, Hubert Hřebabecký, and Antonín Holý. "Preparation of 5-Benzyluracil and 5-Benzylcytosine Nucleosides as Potential Inhibitors of Uridine Phosphorylase." Collection of Czechoslovak Chemical Communications 61, no. 4 (1996): 627–44. http://dx.doi.org/10.1135/cccc19960627.

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Reaction of 3,4,6-tri-O-acetyl-2-deoxyglucopyranosyl bromide (1) with silylated 5-benzyluracil and subsequent ammonolysis afforded α- and β-anomers of 5-benzyl-1-(2-deoxy-D-glucopyranosyl)uracil (2 and 3). Under catalysis with tin tetrachloride, silylated 5-benzyluracil reacted with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose to give 2',3',5'-tri-O-benzoyl-5-benzyluridine (10), which was converted into the 4-thio derivative 11 by reaction with Lawesson reagent. Debenzoylation of compound 11 afforded 5-benzyl-4-thiouridine (12), whereas its reaction with methyl iodide and deblocking gave 4-methylthiopyrimidine nucleoside 14. Amonolysis of derivative 12 at elevated temperature afforded 5-benzylcytidine (15). This reacted with thionyl chloride at room temperature to give cyclic sulfite 16 which on heating at 100 °C in dimethylformamide was converted into 5-benzyl-2,2'-cyclocytidine (17). Mild alkaline hydrolysis of compound 17 afforded 1-(β-D-arabinofuranosyl)-5-benzylcytosine (18). With boiling thionyl chloride, compound 15 formed 2',3'-cyclic sulfite 19 which on alkaline hydrolysis gave 5-benzyl-5'-chloro-5'-deoxycytidine (20). Compound 20 was reduced with tributylstannane to 5-benzyl-5'-deoxycytidine (21). Reaction of silylated 5-benzyluracil with 2-deoxy-3,5-bis(O-p-toluoyl)-D-ribofuranosyl chloride, catalyzed with mercury(II) bromide, afforded 5-benzyl-2'-deoxy-3',5'-bis(O-p-toluoyl)uridine (22) and its α-anomer 23. With Lawesson reagent, compound 22 gave 5-benzyl-4-thiouracil derivative 24 which was ammonolyzed to give 5-benzyl-2'-deoxycytidine (25). Analogously, compound 23 was converted into 5-benzyl-2-deoxy-α-cytidine (27). 5'-O-Benzoyl-5-benzyluridine (29) was converted into the 2,2'-anhydro derivative 30 which on reaction with hydrogen chloride afforded 3'-chloro-3'-deoxynucleoside 31. This compound was reduced with tributylstannane and the obtained 2'-deoxynucleoside 32 on treatment with thionyl chloride gave a mixture of erythro- and threo-3'-chloro-2',3'-dideoxynucleosides (33 and 34, respectively) which were reduced to 5'-O-benzoyl-5-benzyl-2',3'-dideoxyuridine (35). Compound 35 reacted with Lawesson reagent under formation of 4-thiouracil derivative 36 and this was deblocked to 5-benzyl-4-thio-2',3'-dideoxyuridine (37). On heating with ammonia, compound 37 was converted into 5-benzyl-2',3'-dideoxycytidine (38). Reaction of 4-thiouracil derivative with methyl iodide and subsequent hydrazinolysis afforded 4-hydrazino derivative 40 which was heated with silver oxide in ethanol to give a mixture of anomeric 5-benzyl-1-(2,3-dideoxyribofuranosyl)-2(1H)-pyrimidinones (42).

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42

Pearlman, Bruce A., Sterling R. Putt, and Jeffrey A. Fleming. "Olefin synthesis by reaction of stabilized carbanions with carbene equivalents. 1. Use of (iodomethyl)tributylstannane for methylenation of sulfones." Journal of Organic Chemistry 50, no. 19 (September 1985): 3622–24. http://dx.doi.org/10.1021/jo00219a037.

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Pearlman, Bruce A., Sterling R. Putt, and Jeffrey A. Fleming. "Olefin synthesis by reaction of stabilized carbanions with carbene equivalents. 2. Use of (iodomethyl)tributylstannane for methylenation of nitriles." Journal of Organic Chemistry 50, no. 19 (September 1985): 3625–26. http://dx.doi.org/10.1021/jo00219a038.

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Ishizaki, Miyuki, and Osamu Hoshino. "ChemInform Abstract: Unprecedented Cesium and Potassium Fluoride Catalyzed Trialkylsilylation and Tributylstannylation of Terminal Alkynes with Trifluoromethyl-Trialkylsilanes and -Tributylstannane." ChemInform 32, no. 10 (March 6, 2001): no. http://dx.doi.org/10.1002/chin.200110067.

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Liu, Qibo, and Donald J. Burton. "ChemInform Abstract: Stereoselective Preparation of (E)-(1,2-Difluoro-1,2-ethenediyl) Bis[tributylstannane] and Stereospecific Synthesis of (E)-1,2-Difluorostilbenes." ChemInform 33, no. 40 (May 19, 2010): no. http://dx.doi.org/10.1002/chin.200240176.

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Roush, William R., and Michael S. VanNieuwenhze. "[(Z)-.gamma.-[(Diisopropylidene-.alpha.-D-mannopyranosyl)oxy]allyl]tributylstannane: A New Chiral Reagent for the Asymmetric .alpha.-Hydroxyallylation of Aldehydes." Journal of the American Chemical Society 116, no. 19 (September 1994): 8536–43. http://dx.doi.org/10.1021/ja00098a014.

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Guerra, F. M., M. R. Mish, and E. M. Carreira. "Versatile, Diastereoselective Additions of Silyl Ketene Acetals, Allyl Tributylstannane, and Me3SiCN toN-Acyl Pyrazolines: Asymmetric Synthesis of Densely Functionalized Pyrazolidines." Organic Letters 2, no. 26 (December 2000): 4265–67. http://dx.doi.org/10.1021/ol006873f.

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Meurice, Jean-Charles, Martine Vallier, Max Ratier, Jean-Georges Duboudin, and Michel Pétraud. "On the chemospecificity of the double stannylation and double hydrostannation of terminal alkynes by the tributylstannane in the presence of thiol." Journal of Organometallic Chemistry 542, no. 1 (September 1997): 67–73. http://dx.doi.org/10.1016/s0022-328x(97)00283-0.

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ROUSH, W. R., and M. S. VANNIEUWENHZE. "ChemInform Abstract: ((Z)-γ-((Diisopropylidene-α-D-mannopyranosyl)oxy)allyl)- tributylstannane: A New Chiral Reagent for the Asymmetric α- Hydroxyallylation of Aldehydes." ChemInform 26, no. 16 (April 18, 1995): no. http://dx.doi.org/10.1002/chin.199516027.

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Quirante, Josefina, Carmen Escolano, Faïza Diaba, and Josep Bonjoch. "Radical promoted cyclisations of trichloroacetamides with silyl enol ethers and enol acetates: the role of the hydride reagent [tris(trimethylsilyl)silane vs. tributylstannane]." Journal of the Chemical Society, Perkin Transactions 1, no. 9 (1999): 1157–62. http://dx.doi.org/10.1039/a900952c.

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