IPy 2 BF 4 -Mediated Glycosylation and Glycosyl Fluoride Formation

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 predominan...

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Bibliographic Details
Published in:European Journal of Organic Chemistry
Main Authors: Huang, Kuo-Ting, Winssinger, Nicolas
Format: Article in Journal/Newspaper
Language:English
Published: 2007
Subjects:
Carbohydrates
Glycosylation
Thioglycosides
Iodine
IPY
Online Access:https://archive-ouverte.unige.ch/unige:24446
Description
Summary: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.

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