4-O-Benzyl-23-O-isopropylidene-L-threose: A useful building block for stereoselective synthesis of monosaccharides

Teruaki Mukaiyama, Keisuke Suzuki, Tohru Yamada, Fujio Tabusa

Research output: Contribution to journalArticle

155 Citations (Scopus)

Abstract

4-O-Benzyl-23-O-isopropylidene-L-threose readily available from L-tartaric acid is a quite useful four-carbon building block for monosaccharide synthesis. The versatility can be reinforced by the coupled use of stereoselective addition reactions where the suitable choice of organometallics leads to highly anti-selective additions. The building block is particularly useful in the synthesis of rare sugars the versatility of which is demonstrated by the synthesis of some L-sugars as well as the formal total synthesis of polyoxin J in convergent manner.

Original languageEnglish
Pages (from-to)265-276
Number of pages12
JournalTetrahedron
Volume46
Issue number1
DOIs
Publication statusPublished - 1990
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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