Carbohydrate research

Studies on the origin of stereoselectivity in the synthesis of 1, 2-trans glycofuranosyl azides

A Štimac, J Kobe

Index: Stimac, Anton; Kobe, Joze Carbohydrate Research, 2000 , vol. 324, # 3 p. 149 - 160

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Citation Number: 30

Abstract

The stereoselectivity of the 1, 2-trans directed, Lewis acid-catalysed azidation of peracylated furanoses was found to depend on the reactivity of the azide donor (azide nucleophilicity) and the configuration at the anomeric centre relative to the neighbouring 2-O-acyl group. Reactions of 1, 2-trans glycosyl esters with highly nucleophilic azide donors, generated from SnCl4 and Me3SiN3, were stereospecific. The results are interpreted in terms of the rapid ...