Glycosidation-anomerisation reactions of 6,1-anhydroglucopyranuronic acid and anomerisation of beta-D-glucopyranosiduronic acids promoted by SnCl(4)

Chemistry : a European Journal
Colin O'BrienPaul V Murphy

Abstract

The reaction of silylated nucleophiles with 6,1-anhydroglucopyranuronic acid (glucuronic acid 6,1-lactones) catalysed by tin(IV) chloride provides 1,2-trans or 1,2-cis (deoxy)glycosides in a manner dependent on the donor structure. The alpha-glycoside was obtained for reactions of the donor with the 2-acyl group and 2-deoxydonors, whereas the 2-deoxy-2-iodo donor gave the beta-glycoside. Experimental evidence shows that when 1,2-cis-glycoside formation occurs, the anomerisation of initially formed 1,2-trans-glycosides catalysed by SnCl(4) is possible. The anomerisation of beta-D-glucopyranosiduronic acids was found to be faster, in some cases, than anomerisation of related beta-D-glucopyranosiduronic acid esters and beta-D-glucopyranoside derivatives and the rates are dependent on the structure of the aglycon. Moreover, the rates of anomerisation of beta-D-glucopyranuronic acid derivatives can be qualitatively correlated with rates of hydrolysis of beta-D-glucopyranosiduronic acids. Mechanistic possibilities for the reactions are considered.

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Citations

Sep 17, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Wayne PilgrimPaul V Murphy
Jan 23, 2016·Organic Letters·Anthony W McDonaghPaul V Murphy
May 18, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·René RoyHans-Joachim Gabius
Feb 18, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ernest Giralt, Daniele Lo Re
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Related Concepts

Stannic chloride
6,1-anhydroglucopyranuronic acid
Protein Glycosylation
Monosaccharides
Molecular Stereochemistry
Uronic Acids
Tin Compounds

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