New Approaches to the Stereoselective Synthesis of Carbohydrates

Teruaki Mukaiyama, Shin Ichiro Shoda

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

In these years, much interest has been focused on the synthesis of monosaccharides starting from the simple organic molecules, with the development of various highly stereoselective carbon-carbon bond forming reactions of acyclic system. And, recently, convenient syntheses of a variety of monosaccharides are reported using 2, 3-O-isopropylidene-D-glyceraldehyde as 3-carbon building block. Further, a new and potentially useful chiral 4-carbon building block for the L-sugar, 4-0-benzyl-2, 3-O-isopropylidene-L-threose are prepared starting from L-tartaric acid and biologically important L-sugars are also successfully synthesized. Several new glycosylation reactions, which proceed under mild reaction conditions with high stereoselectivity, are exploited; namely, i) the glycosyl fluoride method, ii) the glycoside synthesis by the stereoselective internal cyclizations, and iii) by the direct introduction of alkoxy group to α-position of keto function of sugar.

Original languageEnglish
Pages (from-to)474-478
Number of pages5
JournalJournal of Synthetic Organic Chemistry, Japan
Volume42
Issue number6
DOIs
Publication statusPublished - 1984 Jan

ASJC Scopus subject areas

  • Organic Chemistry

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