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

Hiroomi Tokimoto; Yukari Fujimoto; Koichi Fukase; Shoichi Kusumoto

doi:10.1016/j.tetasy.2004.11.042

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

Hiroomi Tokimoto, Yukari Fujimoto, Koichi Fukase, Shoichi Kusumoto

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

36 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 language	English
Pages (from-to)	441-447
Number of pages	7
Journal	Tetrahedron Asymmetry
Volume	16
Issue number	2
DOIs	https://doi.org/10.1016/j.tetasy.2004.11.042
Publication status	Published - 2005 Jan 24

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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

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.",

author = "Hiroomi Tokimoto and Yukari Fujimoto and Koichi Fukase and Shoichi Kusumoto",

note = "Funding Information: The present work was financially supported in part by the Grant-in-Aid for Scientific Research No. 15310149 from the Japan Society for the Promotion of Science and by the Grant-in-Aid for Creative Scientific Research {\textquoteleft}In vivo Molecular Science for Discovery of New Biofunctions and Pharmaceutical Drugs{\textquoteright} No. 13NP0401 from the Ministry of Education, Science, Sports and Culture, Japan. CPME used in this work was a generous gift of ZEON Cooperation, R&D Center. 15",

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T1 - Stereoselective glycosylation using the long-range effect of a [2-(4-phenylbenzyl)oxycarbonyl]benzoyl group

AU - Tokimoto, Hiroomi

AU - Fujimoto, Yukari

AU - Fukase, Koichi

AU - Kusumoto, Shoichi

N1 - Funding Information: The present work was financially supported in part by the Grant-in-Aid for Scientific Research No. 15310149 from the Japan Society for the Promotion of Science and by the Grant-in-Aid for Creative Scientific Research ‘In vivo Molecular Science for Discovery of New Biofunctions and Pharmaceutical Drugs’ No. 13NP0401 from the Ministry of Education, Science, Sports and Culture, Japan. CPME used in this work was a generous gift of ZEON Cooperation, R&D Center. 15

PY - 2005/1/24

Y1 - 2005/1/24

N2 - 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.

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