IPy<sub>2</sub>BF<sub>4</sub>-Mediated Glycosylation and Glycosyl Fluoride Formation

Huang, Kuo-Ting; Winssinger, Nicolas

doi:10.1002/ejoc.200700038

Scientific article

English

IPy₂BF₄-Mediated Glycosylation and Glycosyl Fluoride Formation

ContributorsHuang, Kuo-Ting; Winssinger, Nicolas

Published inEuropean journal of organic chemistry, vol. 2007, no. 12, p. 1887-1890

Publication date2007

Abstract

A facile method to convert thioglycosides to glycosyl fluorides with Ipy2BF4 (py = pyridine) is presented. Alternatively, activation of thioglycosides with Ipy2BF4 in the presence of acids and glycosyl acceptors led to glycosylation reactions. Perbenzylated (armed) glycosyl donors yielded predominantly the β-anomeric product. This methodology is compatible with one-pot sequential glycosylation.

Keywords

Carbohydrates
Glycosylation
Thioglycosides
Iodine

Affiliation entities

Not a UNIGE publication

Citation (ISO format)

HUANG, Kuo-Ting, WINSSINGER, Nicolas. IPy₂BF₄-Mediated Glycosylation and Glycosyl Fluoride Formation. In: European journal of organic chemistry, 2007, vol. 2007, n° 12, p. 1887–1890. doi: 10.1002/ejoc.200700038

Article (Published version)

Identifiers

PID : unige:24446
DOI : 10.1002/ejoc.200700038

Journal ISSN1099-0690

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IPy2BF4-Mediated Glycosylation and Glycosyl Fluoride Formation

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IPy₂BF₄-Mediated Glycosylation and Glycosyl Fluoride Formation