Glycosidation of 3,4,6-tri-o-benzyl-2-ethenyl-D-glucal - A route to 2-C-(β-methyl)methylene glycosides

Ben Ami Feit, Idil Kasuto Kelson, Anke Gerull, Sarah Abramson, Richard R. Schmidt

Research output: Contribution to journalArticlepeer-review

Abstract

Monosaccharidic and disaccharidic 2-C-(β-methyl)methylene glycosides were synthesized by an electrophilic conjugate addition reaction of ROH-type compounds in the presence of Ph3+PH Br- to 2-ethenyl-3,4,6-tri-O-benzyl-D-glucal 1, functioning as a model glycosyl donor. This 2-vinyl glucal derivative represents a series of 2-vinyl and 2-butadienyl glycals, prepared by Wittig-type methylenation of pyranosidic conjugated enals, derived from glucal, galactal and lactal. The exo-(β-methyl)methylene group paves the way for further chemical transformations.

Original languageEnglish
Pages (from-to)661-675
Number of pages15
JournalJournal of Carbohydrate Chemistry
Volume19
Issue number6
DOIs
StatePublished - 2000

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