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Carbohydrate-2-deoxy-2-phosphonates: Simple Synthesis and Horner–Emmons Reaction

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  • This research was generously supported by the Deutsche Forschungsgemeinschaft (Li 556/7-3).

Abstract

Phosphorus meets carbohydrates: Dimethyl phosphite reacts with ceric(IV) ammonium nitrate (CAN) to give phosphonyl radicals that add to glycals 1. The derivatives 2 were isolated in high yields and during a subsequent Horner–Emmons reaction underwent an interesting elimination to give 3,6-dihydro-2H-pyrans 3. The short sequence with simple precursors is applicable to the transformation of hexoses, pentoses, and disaccharides. Bn=benzyl.

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