Synthesis ofO-glycopyranosyl-N-hydroxysuccinimides of glucose and lactose and their opening by nucleophiles into prespacer glycosides

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Abstract
O-Glycopyranosyl-N-hydroxysuccinimides of glucose and lactose have been synthesized. Peracetylated sugars, acetobromo sugars and benzoylated thioethyl glycosides have been used as precursors. With boron trifluoride etherate in dichloromethane, peracetylated sugars gave predominantly the β anomer. Trimethylsilyl trifluoromethanesulfonate in nitromethane, however, gave predominantly the α anomer. Treatment of the acetylatedO-glucopyranosyl-N-hydroxysuccinimide with various nucleophiles (methoxide, hydroxide and pentylamine) gave the corresponding deacetylatedN-(succinyl)glucopyranosylhydroxylamines in almost quantitative yield. These derivatives are suitable for the formation of glycoconjugates or attachment of carbohydrates to solid phases using the opened succinimide as linking arm.