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Journal articles on the topic 'Allyl glycosides'

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Published: 6 September 2023

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1

Pal, Rita, Anupama Das, and Narayanaswamy Jayaraman. "One-pot oligosaccharide synthesis: latent-active method of glycosylations and radical halogenation activation of allyl glycosides." Pure and Applied Chemistry 91, no. 9 (September 25, 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, and 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, no. 22 (1997): 3357–60. http://dx.doi.org/10.1039/a704703g.

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3

Krähmer, Ralf, Lothar Hennig, Matthias Findeisen, Dietrich Müller, and Peter Welzel. "Oxidative deprotection of allyl glycosides." Tetrahedron 54, no. 36 (September 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, and Nikolay E. Nifant’ev. "Synthesis of spacer-armed glycosides using azidophenylselenylation of allyl glycosides." Mendeleev Communications 8, no. 1 (January 1998): 9–11. http://dx.doi.org/10.1070/mc1998v008n01abeh000887.

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5

Wang, Pengfei, Pranab Haldar, Yun Wang, and Huayou Hu. "Simple Glycosylation Reaction of Allyl Glycosides." Journal of Organic Chemistry 72, no. 15 (July 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, and Jacques H. van Boom. "Selective Cross‐Metathesis ofC‐Allyl‐Glycosides." Journal of Carbohydrate Chemistry 24, no. 4-6 (August 2005): 335–51. http://dx.doi.org/10.1080/07328300500174887.

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7

GIBSON, R. R., R. P. DICKINSON, and G. J. BOONS. "ChemInform Abstract: Vinyl Glycosides in Oligosaccharide Synthesis. Part 4. Glycosidase-Catalyzed Preparation of Substituted Allyl Glycosides." ChemInform 29, no. 14 (June 23, 2010): no. http://dx.doi.org/10.1002/chin.199814171.

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8

Hu, Yun-Jin, Romyr Dominique, Sanjoy Kumar Das, and René Roy. "A facile new procedure for the deprotection of allyl ethers under mild conditions." Canadian Journal of Chemistry 78, no. 6 (June 1, 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, and P. WELZEL. "ChemInform Abstract: Oxidative Deprotection of Allyl Glycosides." ChemInform 29, no. 50 (June 18, 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, and N. E. NIFANT'EV. "ChemInform Abstract: Synthesis of Spacer-Armed Glycosides Using Azidophenylselenylation of Allyl Glycosides." ChemInform 29, no. 30 (June 20, 2010): no. http://dx.doi.org/10.1002/chin.199830240.

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11

Pal, Rita, Anupama Das, and Narayanaswamy Jayaraman. "Radical halogenation-mediated latent–active glycosylations of allyl glycosides." Chemical Communications 54, no. 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, and Bahar A. Schmidtmann. "Studies on the Stereoselective Synthesis ofC-Allyl Glycosides." Organic Letters 10, no. 21 (November 6, 2008): 4727–30. http://dx.doi.org/10.1021/ol801710s.

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13

Bellucci, Giuseppe, Cinzia Chiappe, and Felicia D'Andrea. "Diastereoselective bromination of allyl glycosides using tetrabutylammonium tribromide." Tetrahedron: Asymmetry 6, no. 1 (January 1995): 221–30. http://dx.doi.org/10.1016/0957-4166(94)00378-o.

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14

Das, Anupama, and Narayanaswamy Jayaraman. "Carbon tetrachloride-free allylic halogenation-mediated glycosylations of allyl glycosides." Organic & Biomolecular Chemistry 19, no. 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, and Jianbo Zhang. "Progress in the Synthesis of 2,3-unsaturated Glycosides." Current Organic Chemistry 24, no. 2 (April 15, 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, and Peter Welzel. "A new method for the cleavage of allyl glycosides." Tetrahedron Letters 34, no. 37 (September 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, and Xue-Wei Liu. "A highly efficient dual catalysis approach for C-glycosylation: addition of (o-azaaryl)carboxaldehyde to glycals." Chem. Commun. 50, no. 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, and Johannes F. G. Vliegenthart. "Thiol addition to protected allyl glycosides: An improved method for the preparation of spacer-arm glycosides." Carbohydrate Research 300, no. 4 (May 1997): 369–73. http://dx.doi.org/10.1016/s0008-6215(97)00074-8.

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19

Boons, Geert-Jan, and Stephen Isles. "Vinyl Glycosides in Oligosaccharide Synthesis. 2. The Use of Allyl and Vinyl Glycosides in Oligosaccharide Synthesis." Journal of Organic Chemistry 61, no. 13 (January 1996): 4262–71. http://dx.doi.org/10.1021/jo960131b.

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20

Panchadhayee, Rajib, and Anup Kumar Misra. "N-Bromosuccinimide-Mediated Conversion of Allyl Glycosides to Glycosyl Hemiacetals." Journal of Carbohydrate Chemistry 29, no. 2 (March 22, 2010): 76–83. http://dx.doi.org/10.1080/07328301003664887.

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21

Xie, Juan, and Jean-Marc Valéry. "INVESTIGATION OF THE SHARPLESS ASYMMETRIC AMINOHYDROXYLATION WITH C-ALLYL GLYCOSIDES." Journal of Carbohydrate Chemistry 20, no. 6 (July 31, 2001): 441–45. http://dx.doi.org/10.1081/car-100106927.

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22

BELLUCCI, G., C. CHIAPPE, and F. D'ANDREA. "ChemInform Abstract: Diastereoselective Bromination of Allyl Glycosides Using Tetrabutylammonium Tribromide." ChemInform 26, no. 27 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199527050.

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23

Kánya, Nándor, Sándor Kun, and 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, no. 22 (November 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, and 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 (December 22, 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, and Subhash C. Taneja. "2,3-Unsaturated Allyl Glycosides as Glycosyl Donors for Selective α-Glycosylation." Journal of Organic Chemistry 76, no. 9 (May 6, 2011): 3506–10. http://dx.doi.org/10.1021/jo102333x.

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26

Khamsi, Jamal, Roger A. Ashmus, Nathaniel S. Schocker, and Katja Michael. "A high-yielding synthesis of allyl glycosides from peracetylated glycosyl donors." Carbohydrate Research 357 (August 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, and P. WELZEL. "ChemInform Abstract: A New Method for the Cleavage of Allyl Glycosides." ChemInform 25, no. 4 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199404250.

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28

Lopez, J. Cristobal, Fernando Lobo, Silvia Miranda, Clara Uriel, and Ana M. Gomez. "Ferrier–Nicholas pyranosidic cations: application to diversity-oriented synthesis." Pure and Applied Chemistry 86, no. 9 (September 19, 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., and S. ISLES. "ChemInform Abstract: Vinyl Glycosides in Oligosaccharide Synthesis. Part 2. The Use of Allyl and Vinyl Glycosides in Oligosaccharide Synthesis." ChemInform 27, no. 45 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199645246.

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30

Hu, Yun-Jin, and Rene´ Roy. "Cross-metathesis of N-alkenyl peptoids with O- or C-allyl glycosides." Tetrahedron Letters 40, no. 17 (April 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, and René Roy. "Subtle Stereochemical and Electronic Effects in Iridium-Catalyzed Isomerization ofC-Allyl Glycosides." Organic Letters 8, no. 13 (June 2006): 2691–94. http://dx.doi.org/10.1021/ol060671n.

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32

Xie, Juan, and Jean-Marc Valery. "ChemInform Abstract: Investigation of the Sharpless Asymmetric Aminohydroxylation with C-Allyl Glycosides." ChemInform 33, no. 9 (May 22, 2010): no. http://dx.doi.org/10.1002/chin.200209199.

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33

Panchadhayee, Rajib, and Anup Kumar Misra. "ChemInform Abstract: N-Bromosuccinimide-Mediated Conversion of Allyl Glycosides to Glycosyl Hemiacetals." ChemInform 41, no. 47 (October 28, 2010): no. http://dx.doi.org/10.1002/chin.201047191.

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34

Husein, Husein A., Dhurgham A. H. Alhasan, and Majid A. Z. Albadry. "In Vitro Antimicrobial Activity of Aqueous-Methanolic Extract of Populus sp. Leaves." Basrah Journal of Agricultural Sciences 31, no. 2 (February 8, 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, and Subhash C. Taneja. "ChemInform Abstract: 2,3-Unsaturated Allyl Glycosides as Glycosyl Donors for Selective α-Glycosylation." ChemInform 42, no. 32 (July 14, 2011): no. http://dx.doi.org/10.1002/chin.201132190.

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36

Finch, Paul, George M. Iskander, and Aloysius H. Siriwardena. "Convenient syntheses of 2,3,5-tri-O-benzyl-arabino- and −ribofuranoses via their allyl glycosides." Carbohydrate Research 210 (March 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, and Patrick J. Brennan. "Synthesis of allyl glycosides for conversion into neoglycoproteins bearing epitopes of mycobacterial glycolipid antigens." Carbohydrate Research 216 (September 1992): 337–55. http://dx.doi.org/10.1016/0008-6215(92)84172-o.

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38

Cardona, Francisco, and Barbara La Ferla. "Synthesis of C-Glycoconjugates from Readily Available Unprotected C-Allyl Glycosides by Chemoselective Ligation." Journal of Carbohydrate Chemistry 27, no. 4 (May 2008): 203–13. http://dx.doi.org/10.1080/07328300802082457.

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39

Araki, Younosuke, Naoki Kobayashi, Kazuko Watanabe, and Yoshiharu Ishido. "Synthesis of Glycosyl Cyanides andC-Allyl Glycosides by the use of Glycosyl Fluoride Derivatives." Journal of Carbohydrate Chemistry 4, no. 4 (December 1985): 565–85. http://dx.doi.org/10.1080/07328308508082677.

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40

Hu, Yun-Jin, and Rene Roy. "ChemInform Abstract: Cross-Methathesis of N-Alkenyl Peptoids with O- or C-Allyl Glycosides." ChemInform 30, no. 30 (June 14, 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, and 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, no. 4 (April 1, 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 CO 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, and Uwe Klinkhammer. "The Allyl Ester as Carboxy-Protecting Group in the Stereoselective Construction of Neuraminic-Acid Glycosides." Helvetica Chimica Acta 71, no. 8 (December 14, 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, and Henrik Stålbrand. "Transglycosylation by β-mannanase TrMan5A variants and enzyme synergy for synthesis of allyl glycosides from galactomannan." Process Biochemistry 112 (January 2022): 154–66. http://dx.doi.org/10.1016/j.procbio.2021.11.028.

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44

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

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45

Auzanneau, F. "Efficient, convergent syntheses of oligosaccharide allyl glycosides corresponding to the Streptococcus Group A cell-wall polysaccharide." Carbohydrate Research 291, no. 1 (September 23, 1996): 21–41. http://dx.doi.org/10.1016/0008-6215(96)00152-8.

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46

FINCH, P., G. M. ISKANDER, and A. H. SIRIWARDENA. "ChemInform Abstract: Convenient Syntheses of 2,3,5-Tri-O-benzyl-arabino- and -ribofuranoses via Their Allyl Glycosides." ChemInform 23, no. 7 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199207257.

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47

Kononov, Leonid O., Göran Magnusson, Marina I. Ferrero, Cesare Rol, Giovanni V. Sebastiani, George W. Francis, József Szúnyog, and Bengt Långström. "Synthesis of Methyl and Allyl alpha-Glycosides of N-Acetylneuraminic Acid in the Absence of Added Promoter." Acta Chemica Scandinavica 52 (1998): 141–44. http://dx.doi.org/10.3891/acta.chem.scand.52-0141.

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48

Di Bussolo, Valeria, Annalisa Fiasella, Maria Rosaria Romano, Lucilla Favero, Mauro Pineschi, and Paolo Crotti. "Stereoselective Synthesis of 2,3-Unsaturated-aza-O-glycosides via New DiastereoisomericN-Cbz-imino Glycal-Derived Allyl Epoxides†." Organic Letters 9, no. 22 (October 2007): 4479–82. http://dx.doi.org/10.1021/ol701836a.

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49

Eichler, Eva, Jan Kihlberg, and David R. Bundle. "Access to fluorescent probes via allyl glycosides: the synthesis of aBrucella trisaccharide epitope linked to a coumarin." Glycoconjugate Journal 8, no. 2 (April 1991): 69–74. http://dx.doi.org/10.1007/bf00731014.

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50

Pastore, Antonello, Matteo Adinolfi, and 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, no. 36 (December 2008): 6206–12. http://dx.doi.org/10.1002/ejoc.200800914.

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