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Artykuły w czasopismach na temat „Allyl glycosides”

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Data publikacji: 6 września 2023

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1

Pal, Rita, Anupama Das i Narayanaswamy Jayaraman. "One-pot oligosaccharide synthesis: latent-active method of glycosylations and radical halogenation activation of allyl glycosides". Pure and Applied Chemistry 91, nr 9 (25.09.2019): 1451–70. http://dx.doi.org/10.1515/pac-2019-0306.

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Abstract Chemical glycosylations occupy a central importance to synthesize tailor-made oligo- and polysaccharides of functional importance. Generation of the oxocarbenium ion or the glycosyl cation is the method of choice in order to form the glycosidic bond interconnecting a glycosyl moiety with a glycosyl/aglycosyl moiety. A number of elegant methods have been devised that allow the glycosyl cation formation in a fairly stream-lined manner to a large extent. The latent-active method provides a powerful approach in the protecting group controlled glycosylations. In this context, allyl glycosides have been developed to meet the requirement of latent-active reactivities under appropriate glycosylation conditions. Radical halogenation provides a newer route of activation of allyl glycosides to an activated allylic glycoside. Such an allylic halide activation subjects the glycoside reactive under acid catalysis, leading to the conversion to a glycosyl cation and subsequent glycosylation with a number of acceptors. The complete anomeric selectivity favoring the 1,2-trans-anomeric glycosides points to the possibility of a preferred conformation of the glycosyl cation. This article discusses about advancements in the selectivity of glycosylations, followed by delineating the allylic halogenation of allyl glycoside as a glycosylation method and demonstrates synthesis of a repertoire of di- and trisaccharides, including xylosides, with varied protecting groups.
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2

Gibson, Robin R., Roger P. Dickinson i Geert-Jan Boons. "Vinyl glycosides in oligosaccharide synthesis (part 4): glycosidase-catalysed preparation of substituted allyl glycosides". Journal of the Chemical Society, Perkin Transactions 1, nr 22 (1997): 3357–60. http://dx.doi.org/10.1039/a704703g.

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3

Krähmer, Ralf, Lothar Hennig, Matthias Findeisen, Dietrich Müller i Peter Welzel. "Oxidative deprotection of allyl glycosides". Tetrahedron 54, nr 36 (wrzesień 1998): 10753–60. http://dx.doi.org/10.1016/s0040-4020(98)00640-1.

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4

Sherman, Andrei A., Leonid O. Kononov, Alexander S. Shashkov, Georgij V. Zatonsky i Nikolay E. Nifant’ev. "Synthesis of spacer-armed glycosides using azidophenylselenylation of allyl glycosides". Mendeleev Communications 8, nr 1 (styczeń 1998): 9–11. http://dx.doi.org/10.1070/mc1998v008n01abeh000887.

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5

Wang, Pengfei, Pranab Haldar, Yun Wang i Huayou Hu. "Simple Glycosylation Reaction of Allyl Glycosides". Journal of Organic Chemistry 72, nr 15 (lipiec 2007): 5870–73. http://dx.doi.org/10.1021/jo070512x.

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6

Timmer, Mattie S. M., Marta Vinciano Chumillas, Wilma E. Donker‐Koopman, Johannes M. F. G. Aerts, Gijsbert A. van derMarel, Herman S. Overkleeft i Jacques H. van Boom. "Selective Cross‐Metathesis ofC‐Allyl‐Glycosides". Journal of Carbohydrate Chemistry 24, nr 4-6 (sierpień 2005): 335–51. http://dx.doi.org/10.1080/07328300500174887.

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7

GIBSON, R. R., R. P. DICKINSON i G. J. BOONS. "ChemInform Abstract: Vinyl Glycosides in Oligosaccharide Synthesis. Part 4. Glycosidase-Catalyzed Preparation of Substituted Allyl Glycosides." ChemInform 29, nr 14 (23.06.2010): no. http://dx.doi.org/10.1002/chin.199814171.

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8

Hu, Yun-Jin, Romyr Dominique, Sanjoy Kumar Das i René Roy. "A facile new procedure for the deprotection of allyl ethers under mild conditions". Canadian Journal of Chemistry 78, nr 6 (1.06.2000): 838–45. http://dx.doi.org/10.1139/v00-073.

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A novel isomerization of O-allyl glycosides into prop-1-enyl glycosides was observed instead of cross-metathesis during an olefin metathesis reaction using Grubbs' ruthenium benzylidene catalyst (Cy3P)2RuCl2=CHPh (1), N-allyltritylamine, and N,N-diisopropylethylamine as necessary auxiliary reagents. In the search for a better catalytic system, it has been found that dichlorotris(triphenylphosphine)ruthenium(II), [(C6H5)3P]3RuCl2, (2) was much more efficient for the isomerization of allylic ethers. The labile prop-1-enyl group was easily hydrolyzed using HgCl2-HgO and the hemiacetals (25-32) were isolated in excellent yields (ca. 90%).Key words: allyl ether, carbohydrate, Grubbs' catalyst, isomerization, metathesis, deprotection.
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9

KRAEHMER, R., L. HENNIG, M. FINDEISEN, D. MUELLER i P. WELZEL. "ChemInform Abstract: Oxidative Deprotection of Allyl Glycosides." ChemInform 29, nr 50 (18.06.2010): no. http://dx.doi.org/10.1002/chin.199850242.

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10

SHERMAN, A. A., L. O. KONONOV, A. S. SHASHKOV, G. V. ZATONSKY i N. E. NIFANT'EV. "ChemInform Abstract: Synthesis of Spacer-Armed Glycosides Using Azidophenylselenylation of Allyl Glycosides." ChemInform 29, nr 30 (20.06.2010): no. http://dx.doi.org/10.1002/chin.199830240.

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11

Pal, Rita, Anupama Das i Narayanaswamy Jayaraman. "Radical halogenation-mediated latent–active glycosylations of allyl glycosides". Chemical Communications 54, nr 6 (2018): 588–90. http://dx.doi.org/10.1039/c7cc07332a.

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Radical halogenation-mediated glycosylation using allyl glycosides as donors and as acceptors emerges to be an efficient and hither-to unknown glycosylation method, adhering to the concept of the latent–active methodology.
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12

McGarvey, Glenn J., Christopher A. LeClair i Bahar A. Schmidtmann. "Studies on the Stereoselective Synthesis ofC-Allyl Glycosides". Organic Letters 10, nr 21 (6.11.2008): 4727–30. http://dx.doi.org/10.1021/ol801710s.

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13

Bellucci, Giuseppe, Cinzia Chiappe i Felicia D'Andrea. "Diastereoselective bromination of allyl glycosides using tetrabutylammonium tribromide". Tetrahedron: Asymmetry 6, nr 1 (styczeń 1995): 221–30. http://dx.doi.org/10.1016/0957-4166(94)00378-o.

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14

Das, Anupama, i Narayanaswamy Jayaraman. "Carbon tetrachloride-free allylic halogenation-mediated glycosylations of allyl glycosides". Organic & Biomolecular Chemistry 19, nr 42 (2021): 9318–25. http://dx.doi.org/10.1039/d1ob01298c.

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A one-pot CCl4-free allylic halide activation of allyl glycosides, followed by glycosylation with acceptors, is conducted in a latent-active manner. PhCF3 as the solvent and TMSOTf/Tf2O as the promoter system are optimal for the reaction.
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15

Jiang, Nan, Zhengliang Wu, Youxian Dong, Xiaoxia Xu, Xiaxia Liu i Jianbo Zhang. "Progress in the Synthesis of 2,3-unsaturated Glycosides". Current Organic Chemistry 24, nr 2 (15.04.2020): 184–99. http://dx.doi.org/10.2174/1385272824666200130111142.

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The substitution reaction of glycal (1,2-unsaturated cyclic carbohydrate derivative) at C1 by allyl rearrangement in the presence of a catalyst is called Ferrier type-I rearrangement. 2,3-Unsaturated glycosides are usually obtained from glycals through Ferrier type-I rearrangement, and their potential biological activities have gradually attracted widespread attention of researchers. This review summarizes recent advances (2009- present) in the application of various types of catalysts to Ferrier type-I rearrangement reactions, including their synthesis, mechanism, and application of 2, 3-unsaturated glycosides.
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16

Lüning, Joachim, Uwe Möller, Norbert Debski i Peter Welzel. "A new method for the cleavage of allyl glycosides". Tetrahedron Letters 34, nr 37 (wrzesień 1993): 5871–74. http://dx.doi.org/10.1016/s0040-4039(00)73801-9.

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17

Bai, Yaguang, Wei Lin Leng, Yongxin Li i Xue-Wei Liu. "A highly efficient dual catalysis approach for C-glycosylation: addition of (o-azaaryl)carboxaldehyde to glycals". Chem. Commun. 50, nr 87 (2014): 13391–93. http://dx.doi.org/10.1039/c4cc06111j.

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Dual catalysis by concurrent activation of glycals and (O-azaaryl)-carboxaldehydes using palladium and N-heterocyclic carbene has been developed. This activation through the formation of the Breslow intermediate and a π-allyl Pd complex is a novel and efficient approach to yield C-glycosides with yields up to 85%.
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18

van Seeventer, Paul B., Johannes A. L. M. van Dorst, John F. Siemerink, Johannis P. Kamerling i Johannes F. G. Vliegenthart. "Thiol addition to protected allyl glycosides: An improved method for the preparation of spacer-arm glycosides". Carbohydrate Research 300, nr 4 (maj 1997): 369–73. http://dx.doi.org/10.1016/s0008-6215(97)00074-8.

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19

Boons, Geert-Jan, i Stephen Isles. "Vinyl Glycosides in Oligosaccharide Synthesis. 2. The Use of Allyl and Vinyl Glycosides in Oligosaccharide Synthesis". Journal of Organic Chemistry 61, nr 13 (styczeń 1996): 4262–71. http://dx.doi.org/10.1021/jo960131b.

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20

Panchadhayee, Rajib, i Anup Kumar Misra. "N-Bromosuccinimide-Mediated Conversion of Allyl Glycosides to Glycosyl Hemiacetals". Journal of Carbohydrate Chemistry 29, nr 2 (22.03.2010): 76–83. http://dx.doi.org/10.1080/07328301003664887.

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21

Xie, Juan, i Jean-Marc Valéry. "INVESTIGATION OF THE SHARPLESS ASYMMETRIC AMINOHYDROXYLATION WITH C-ALLYL GLYCOSIDES". Journal of Carbohydrate Chemistry 20, nr 6 (31.07.2001): 441–45. http://dx.doi.org/10.1081/car-100106927.

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22

BELLUCCI, G., C. CHIAPPE i F. D'ANDREA. "ChemInform Abstract: Diastereoselective Bromination of Allyl Glycosides Using Tetrabutylammonium Tribromide." ChemInform 26, nr 27 (17.08.2010): no. http://dx.doi.org/10.1002/chin.199527050.

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23

Kánya, Nándor, Sándor Kun i László Somsák. "Glycopyranosylidene-Spiro-Morpholinones: Evaluation of the Synthetic Possibilities Based on Glyculosonamide Derivatives and a New Method for the Construction of the Morpholine Ring". Molecules 27, nr 22 (11.11.2022): 7785. http://dx.doi.org/10.3390/molecules27227785.

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Glycosylidene-spiro-morpholin(on)es are scarcely described skeletons in the literature. In this work, we have systematically explored the synthetic routes towards such morpholinones based on the reactions of O-peracylated hept-2-ulopyranosonamide derivatives of D-gluco and D-galacto configuration. Koenigs–Knorr type glycosylation of 2-chloroethanol, allylic and propargylic alcohols by (glyculosylbromide)onamides furnished the expected glycosides. The 2-chloroethyl glycosides were ring closed to the corresponding spiro-morpholinones by treatment with K2CO3. The (allyl glyculosid)onamides gave diastereomeric mixtures of spiro-5-hydroxymorpholinones by ozonolysis and 5-iodomethylmorpholinones under iodonium ion mediated conditions. The ozonolytic method has not yet been known for the construction of morpholine rings, therefore, it was also extended to O-allyl mandelamide. The 5-hydroxymorpholinones were subjected to oxidation and acid catalyzed elimination reactions to give the corresponding morpholine-3,5-dions and 5,6-didehydro-morpholin-3-ones, respectively. Base induced elimination of the 5-iodomethylmorpholinones gave 5-methyl-2H-1,4-oxazin-3(4H)-ones. O-Acyl protecting groups of all of the above compounds were removed under Zemplén conditions. Some of the D-gluco configured unprotected compounds were tested as inhibitors of glycogen phosphorylase, but showed no significant effect.
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24

Sommer, Roman, Dirk Hauck, Annabelle Varrot, Anne Imberty, Markus Künzler i Alexander Titz. "O-Alkylated heavy atom carbohydrate probes for protein X-ray crystallography: Studies towards the synthesis of methyl 2-O-methyl-L-selenofucopyranoside". Beilstein Journal of Organic Chemistry 12 (22.12.2016): 2828–33. http://dx.doi.org/10.3762/bjoc.12.282.

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Selenoglycosides are used as reactive glycosyl donors in the syntheses of oligosaccharides. In addition, such heavy atom analogs of natural glycosides are useful tools for structure determination of their lectin receptors using X-ray crystallography. Some lectins, e.g., members of the tectonin family, only bind to carbohydrate epitopes with O-alkylated ring hydroxy groups. In this context, we report the first synthesis of an O-methylated selenoglycoside, specifically methyl 2-O-methyl-L-selenofucopyranoside, a ligand of the lectin tectonin-2 from the mushroom Laccaria bicolor. The synthetic route required a strategic revision and further optimization due to the intrinsic lability of alkyl selenoglycosides, in particular for the labile fucose. Here, we describe a successful synthetic access to methyl 2-O-methyl-L-selenofucopyranoside in 9 linear steps and 26% overall yield starting from allyl L-fucopyranoside.
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25

Kumar, Brijesh, Mushtaq A. Aga, Abdul Rouf, Bhahwal A. Shah i Subhash C. Taneja. "2,3-Unsaturated Allyl Glycosides as Glycosyl Donors for Selective α-Glycosylation". Journal of Organic Chemistry 76, nr 9 (6.05.2011): 3506–10. http://dx.doi.org/10.1021/jo102333x.

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26

Khamsi, Jamal, Roger A. Ashmus, Nathaniel S. Schocker i Katja Michael. "A high-yielding synthesis of allyl glycosides from peracetylated glycosyl donors". Carbohydrate Research 357 (sierpień 2012): 147–50. http://dx.doi.org/10.1016/j.carres.2012.05.008.

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27

LUENING, J., U. MOELLER, N. DEBSKI i P. WELZEL. "ChemInform Abstract: A New Method for the Cleavage of Allyl Glycosides." ChemInform 25, nr 4 (19.08.2010): no. http://dx.doi.org/10.1002/chin.199404250.

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28

Lopez, J. Cristobal, Fernando Lobo, Silvia Miranda, Clara Uriel i Ana M. Gomez. "Ferrier–Nicholas pyranosidic cations: application to diversity-oriented synthesis". Pure and Applied Chemistry 86, nr 9 (19.09.2014): 1357–64. http://dx.doi.org/10.1515/pac-2014-0402.

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AbstractPyranosidic allylic (Ferrier) cations that share dicobalt hexacarbonyl propargyl (Nicholas) stabilization at C-1, can be easily generated by treatment of hexacarbonyldicobalt alkynyl glycals with BF3·OEt2, and display a remarkable reactivity leading to a variety of products. The substituent at O-6 in these glycals plays a pivotal role in directing the outcome of the transformations. Accordingly, 6-O-benzyl or 6-O-allyl groups cause a series of transformations resulting in the stereoselective formation of oxepanes through a process that involves an initial hydride transfer step from the allyl or benzyl substituent to the Ferrier–Nicholas cation. On the contrary, 6-OH derivatives undergo an overall ring contraction to branched tetrahydrofuran derivatives. 6-O-Silyl derivatives, in the presence of heteroaryl nucleophiles, were transformed into C-3 branched bis-C-C-glycosides, containing two of such molecules.
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29

BOONS, G. J., i S. ISLES. "ChemInform Abstract: Vinyl Glycosides in Oligosaccharide Synthesis. Part 2. The Use of Allyl and Vinyl Glycosides in Oligosaccharide Synthesis." ChemInform 27, nr 45 (4.08.2010): no. http://dx.doi.org/10.1002/chin.199645246.

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30

Hu, Yun-Jin, i Rene´ Roy. "Cross-metathesis of N-alkenyl peptoids with O- or C-allyl glycosides". Tetrahedron Letters 40, nr 17 (kwiecień 1999): 3305–8. http://dx.doi.org/10.1016/s0040-4039(99)00481-5.

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31

Patnam, Ramesh, Juan M. Juárez-Ruiz i René Roy. "Subtle Stereochemical and Electronic Effects in Iridium-Catalyzed Isomerization ofC-Allyl Glycosides". Organic Letters 8, nr 13 (czerwiec 2006): 2691–94. http://dx.doi.org/10.1021/ol060671n.

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32

Xie, Juan, i Jean-Marc Valery. "ChemInform Abstract: Investigation of the Sharpless Asymmetric Aminohydroxylation with C-Allyl Glycosides." ChemInform 33, nr 9 (22.05.2010): no. http://dx.doi.org/10.1002/chin.200209199.

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33

Panchadhayee, Rajib, i Anup Kumar Misra. "ChemInform Abstract: N-Bromosuccinimide-Mediated Conversion of Allyl Glycosides to Glycosyl Hemiacetals." ChemInform 41, nr 47 (28.10.2010): no. http://dx.doi.org/10.1002/chin.201047191.

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34

Husein, Husein A., Dhurgham A. H. Alhasan i Majid A. Z. Albadry. "In Vitro Antimicrobial Activity of Aqueous-Methanolic Extract of Populus sp. Leaves". Basrah Journal of Agricultural Sciences 31, nr 2 (8.02.2019): 53–64. http://dx.doi.org/10.37077/25200860.2018.102.

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Plants are a rich source of giving benefit natural products, including antimicrobial agents. The current study was designed to evaluate the antimicrobial activity of Populus sp. leaves that the aqueous methanolic extract (200 mg.ml-1) of the leaves revealed antimicrobial effects against some microbial pathogens in which the highest inhibition zone was recorded against Candida albicans followed by Staphylococcus aureus but no effects on the growth of both Streptococcus mutans and Klebsiella sp. The chemical tests appeared that the extract contains sterols, terpenoids, carbohydrates, glycosides, flavonoids, tannins, proteins, amino acids, and saponins glycosides while alkaloids were not detected. GC-MS analysis detected the aqueous methanolic extract has four compounds are {2-Pyridineacetaldehyde,[2-(2-pyridinyl) ethylidene]hydrazone}, {n-Propylamine, N-acetyl-3-[2-acetyl-3,4,5-trimethoxyphenyl]-},{1-(Methyl propyl)-4-(1’,1’,2’-trichloro-3’-ethyl allyl)benzene} and {1H-Indole, 5- methyl-2-phenyl-}.
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35

Kumar, Brijesh, Mushtaq A. Aga, Abdul Rouf, Bhahwal A. Shah i Subhash C. Taneja. "ChemInform Abstract: 2,3-Unsaturated Allyl Glycosides as Glycosyl Donors for Selective α-Glycosylation." ChemInform 42, nr 32 (14.07.2011): no. http://dx.doi.org/10.1002/chin.201132190.

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36

Finch, Paul, George M. Iskander i Aloysius H. Siriwardena. "Convenient syntheses of 2,3,5-tri-O-benzyl-arabino- and −ribofuranoses via their allyl glycosides". Carbohydrate Research 210 (marzec 1991): 319–25. http://dx.doi.org/10.1016/0008-6215(91)80132-7.

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37

Aspinall, Gerald O., Alexander M. Crane, David W. Gammon, Ibrahim H. Ibrahim, Naveen K. Khare, Delphi Chatterjee, Becky Rivoire i Patrick J. Brennan. "Synthesis of allyl glycosides for conversion into neoglycoproteins bearing epitopes of mycobacterial glycolipid antigens". Carbohydrate Research 216 (wrzesień 1992): 337–55. http://dx.doi.org/10.1016/0008-6215(92)84172-o.

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38

Cardona, Francisco, i Barbara La Ferla. "Synthesis of C-Glycoconjugates from Readily Available Unprotected C-Allyl Glycosides by Chemoselective Ligation". Journal of Carbohydrate Chemistry 27, nr 4 (maj 2008): 203–13. http://dx.doi.org/10.1080/07328300802082457.

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39

Araki, Younosuke, Naoki Kobayashi, Kazuko Watanabe i Yoshiharu Ishido. "Synthesis of Glycosyl Cyanides andC-Allyl Glycosides by the use of Glycosyl Fluoride Derivatives". Journal of Carbohydrate Chemistry 4, nr 4 (grudzień 1985): 565–85. http://dx.doi.org/10.1080/07328308508082677.

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40

Hu, Yun-Jin, i Rene Roy. "ChemInform Abstract: Cross-Methathesis of N-Alkenyl Peptoids with O- or C-Allyl Glycosides." ChemInform 30, nr 30 (14.06.2010): no. http://dx.doi.org/10.1002/chin.199930201.

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41

Wu, An-Tai, Tian Yi, Huawu Shao, Shih-Hsiung Wu i Wei Zou. "Stereoselective synthesis of dioxabicycles from 1-C-allyl-2-O-benzyl-glycosides — An intramolecular cyclization between 2-O-benzyl oxygen and the allyl double bond". Canadian Journal of Chemistry 84, nr 4 (1.04.2006): 597–602. http://dx.doi.org/10.1139/v06-046.

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Addition of a proton to the double bond of 1-C-allyl-O-benzylglycosides gave a 2′-carbonium ion, which in turn reacted intramolecularly, in a regio- and diastereo-selective manner, with the nucleophilic oxygen of the 2-O-benzyl group to form an oxonium intermediate. Subsequent cleavage of the benzyl C—O bond led to dioxabicycles in moderate yields. Surprisingly, opposite diastereoselectivities were observed from 1-C-allylglycofuranosides and 1-C-allylglycopyranosides, which produced 2,2′-trans- and 2,2′-cis-dioxabicycles, respectively.Key words: C-glycoside, olefin, cyclization, oxocarbonium, dioxabicycles.
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42

Kunz, Horst, Herbert Waldmann i Uwe Klinkhammer. "The Allyl Ester as Carboxy-Protecting Group in the Stereoselective Construction of Neuraminic-Acid Glycosides". Helvetica Chimica Acta 71, nr 8 (14.12.1988): 1868–74. http://dx.doi.org/10.1002/hlca.19880710804.

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43

Butler, Samuel J., Simon Birgersson, Mathias Wiemann, Monica Arcos-Hernandez i Henrik Stålbrand. "Transglycosylation by β-mannanase TrMan5A variants and enzyme synergy for synthesis of allyl glycosides from galactomannan". Process Biochemistry 112 (styczeń 2022): 154–66. http://dx.doi.org/10.1016/j.procbio.2021.11.028.

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44

Auzanneau, France-Isabelle, Farzin Forooghian i B. Mario Pinto. "Efficient, convergent syntheses of oligosaccharide allyl glycosides corresponding to the Streptococcus Group A cell-wall polysaccharide". Carbohydrate Research 291 (wrzesień 1996): 21–41. http://dx.doi.org/10.1016/s0008-6215(96)00152-8.

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Eichler, Eva, Jan Kihlberg i David R. Bundle. "Access to fluorescent probes via allyl glycosides: the synthesis of aBrucella trisaccharide epitope linked to a coumarin". Glycoconjugate Journal 8, nr 2 (kwiecień 1991): 69–74. http://dx.doi.org/10.1007/bf00731014.

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Pastore, Antonello, Matteo Adinolfi i Alfonso Iadonisi. "BiBr3-Promoted Activation of Peracetylated Glycosyl Iodides: Straightforward Access to Synthetically Useful 2-O-Deprotected Allyl Glycosides". European Journal of Organic Chemistry 2008, nr 36 (grudzień 2008): 6206–12. http://dx.doi.org/10.1002/ejoc.200800914.

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