General methods for the synthesis of glycopyranosyluronic acid azides

L Ying, J Gervay-Hague

Index: Ying, Laiqiang; Gervay-Hague, Jacquelyn Carbohydrate Research, 2003 , vol. 338, # 9 p. 835 - 841

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Citation Number: 35

Abstract

Per-O-acetylated d-glycopyranoses derived from both mono-and disaccharides were first converted to glycosyl iodides and subsequently reacted with an azide source to achieve the stereoselective synthesis of β-d-glycosyl azides after deacetylation. Low-temperature (4° C) TEMPO oxidation of the monosaccharides provided the corresponding uronic acids, which were purified as the free acids. Oxidation of the lactosyl-and cellobiosyl azides resulted in ...