The reaction of N-dichloromethylene-N,N-dialkylammonium chlorides with free sugars: an efficient synthesis of glycosyl chlorides

Abstract

The treatment of aldose derivatives that are protected at all but the anomeric hydroxy groups with N-dichloromethylene-N,N-dialkylammonium chlorides (alkyl = Me, Et) provides an improved method of preparing the corresponding glycosyl chlorides. Analogous derivatives containing anunprotected C1-C2 diol give 2-O-(N,N-dialkylcarbamoyl)glycosyl chlorides.