Reactivity upon demand: Because of their stability towards acids, bases, and many oxidizing and reducing agents, N-glycosyl amides 1 (see scheme) can be used as anomerically protected carbohydrates. The amide function can be cleaved under mild conditions with Ph3P/CBr4 and the carbohydrate activated for the synthesis of N- and O-glycosides 2. PG=protecting group.
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Pleuß et al. (2003) studied this question.
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