Vinyl glycosides in oligosaccharide synthesis (part 6): 3-Buten-2-YL 2-azido-2-deoxy glycosides and 3-buten-2-YL 2-phthalimido-2-deoxy glycosides as novel glycosyl donors

Yu Bai, Geert Jan Boons*, Andrew Burton, Matthew Johnson, Michael Haller

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

An extension of the latent-active glycosylation strategy is reported whereby 3-buten-2-yl 2-deoxy-2-azidoglycosides and 3-buten-2-yl 2-deoxy-2-phthalimidoglycosides are used as building blocks for the preparation of amino sugar containing oligosaccharides. The allyl moieties of the latent substrates 5, 16 and 19 can be conveniently isomerised by treatment with a catalytic amount of (Ph3P)3RhCl/BuLi to give the active vinyl glycosides 6, 17 and 20 in high yield. These glycosyl donors were successfully used in glycosylations with acceptors 7, 9 and 11. In the case of glycosyl donor 6, the disaccharides 8, 10 and 12 could be obtained as anomeric mixtures or with high α-or β-selectivities depending on the reaction conditions selected. Glycosylations with glycosyl donors 17 and 20 in each case gave solely the β-linked products only in high yields.

Original languageEnglish
Pages (from-to)939-958
Number of pages20
JournalJournal of Carbohydrate Chemistry
Volume19
Issue number7
DOIs
Publication statusPublished - 1 Jan 2000
Externally publishedYes

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