Synthesis of a library of fucopyranosyl-galactopyranosides consisting of a complete set of anomeric configurations and linkage positions

Carbohydrate Research
Isao OhtsukaO Kanie

Abstract

A library composed of a complete set of fucopyranosyl-galactopyranosides was synthesized. A perbenzylated phenylthio fucopyranoside and a series of tri-O-benzyl-galactopyranosyl fluorides having single hydroxyl groups at the 2-, 3-, 4-, and 6-positions were used as the glycosyl donor and glycosyl acceptors, respectively. The chosen set of functionalities at the anomeric centers enabled rapid access to the oligosaccharides based on chemoselective activation. The first coupling reaction was achieved by the action of dimethyl(methylthio)sulfonium trifluoromethanesulfonate (DMTST). The resulting disaccharide fluoride was readily activated by hafnocene bistrifluoromethanesulfonate [Cp2Hf(OTf)2] and glycosidated with n-octanol.

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Citations

Sep 4, 2007·Journal of the American Society for Mass Spectrometry·Shusaku DaikokuOsamu Kanie
Mar 8, 2008·Journal of Mass Spectrometry : JMS·Yuki ShioiriOsamu Kanie
May 19, 2007·Journal of Mass Spectrometry : JMS·Shusaku DaikokuOsamu Kanie
Oct 26, 2016·ChemistryOpen·Rituparna Das, Balaram Mukhopadhyay

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