Carbohydrate research

Conversion of p-methoxyphenyl glycosides into the corresponding glycosyl chlorides and bromides, and into thiophenyl glycosides

Z Zhang, G Magnusson

Index: Zhang, Zhiyuan; Magnusson, Goeran Carbohydrate Research, 1996 , vol. 295, p. 41 - 55

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Citation Number: 87

Abstract

p-Methoxyphenyl (pMP) β-d-glycopyranosides (Glc, Gal, GlcNPhth, GalNPhth, GlcNTroc, Galβ4Glc, Galα4Gal) were prepared from the corresponding 1-O-acetyl sugars in 79–90% yield, using boron trifluoride etherate as promoter. Treatment of the pMP glycosides with acyl chlorides or bromides in the presence of various Lewis acids gave the corresponding glycosyl chlorides and bromides in 81–98% yield. Treatment of the acyl-protected pMP ...