Stereoselective glycosylation using the long-range effect of a [2-(4-phenylbenzyl)oxycarbonyl]benzoyl group

Hiroomi Tokimoto, Yukari Fujimoto, Koichi Fukase, Shoichi Kusumoto

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

Highly α-selective glucosylation was effected by virtue of the solvent effect of cyclopentyl methyl ether and the long-range assistance of bulky 6-O-protective groups. Higher α-selectivity was obtained by the use of this solvent in comparison to conventional diethyl ether. α-Selectivity was further improved with the influence of 6-O-substituents, such as TBDPS and phthaloyl groups, the latter being mono esterified with a bulky alcohol.

Original languageEnglish
Pages (from-to)441-447
Number of pages7
JournalTetrahedron Asymmetry
Volume16
Issue number2
DOIs
Publication statusPublished - 2005 Jan 24
Externally publishedYes

Fingerprint

Glycosylation
Ethers
selectivity
Methyl Ethers
diethyl ether
Ether
ethers
alcohols
Alcohols

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Stereoselective glycosylation using the long-range effect of a [2-(4-phenylbenzyl)oxycarbonyl]benzoyl group. / Tokimoto, Hiroomi; Fujimoto, Yukari; Fukase, Koichi; Kusumoto, Shoichi.

In: Tetrahedron Asymmetry, Vol. 16, No. 2, 24.01.2005, p. 441-447.

Research output: Contribution to journalArticle

Tokimoto, Hiroomi ; Fujimoto, Yukari ; Fukase, Koichi ; Kusumoto, Shoichi. / Stereoselective glycosylation using the long-range effect of a [2-(4-phenylbenzyl)oxycarbonyl]benzoyl group. In: Tetrahedron Asymmetry. 2005 ; Vol. 16, No. 2. pp. 441-447.
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