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

154 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

Fingerprint

Monosaccharides
Carbon
Sugars
Addition reactions
Organometallics
erythrose
propylene
tartaric acid
polyoxin

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

4-O-Benzyl-23-O-isopropylidene-L-threose : A useful building block for stereoselective synthesis of monosaccharides. / Mukaiyama, Teruaki; Suzuki, Keisuke; Yamada, Tohru; Tabusa, Fujio.

In: Tetrahedron, Vol. 46, No. 1, 1990, p. 265-276.

Research output: Contribution to journalArticle

Mukaiyama, Teruaki ; Suzuki, Keisuke ; Yamada, Tohru ; Tabusa, Fujio. / 4-O-Benzyl-23-O-isopropylidene-L-threose : A useful building block for stereoselective synthesis of monosaccharides. In: Tetrahedron. 1990 ; Vol. 46, No. 1. pp. 265-276.
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