An easy access to anomeric glycosyl amides and imines (Schiff bases) via transformation of glycopyranosyl trimethylphosphinimides

The preparation and application of anomeric glycosyl phosphinimides in prep arative synthesis were studied. Starting from the appropriate glycosyl azid es and trialkyl or triaryl phosphines, the corresponding phosphinimides wer e obtained by modified Staudinger reactions. The latter compounds were read ily converted into 1-N-acyl-gluco- and galactopyranosyl amines with high yi elds by applying activated acid derivatives or simple carboxylic acids. 1-N -Alkylidene- or arylidenephosphinimines (Schiff bases) were obtained by mea ns of aza-Wittig reactions using aliphatic or aromatic aldehydes, respectiv ely. (C) 2001 Elsevier Science Ltd. All rights reserved.