Synthesis of 3-O-sulphamoyl glucofuranose derivatives

The synthesis of 3-O-sulphamoyl derivatives of 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose, 1,2-O-isopropylidene-α-D-glucofuranose, and 5,6-di-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose is described. A study of the reactions of carbohydrate chlorosulphates with azide has demonstrated the relative case with which certain chlorosulphonyloxy groups may be converted into azidosulphates. These azidosulphates could have potential synthetic value if a facile method for their conversion into sulphamoyl (aminosulphate) derivatives were available, since some sulphamoyl carbohydrates have been shown to possess antibiotic and antitrypanosomal activity. This report deals with the application of sodium borohydride and platinum oxide-hydrogen to the reduction of some 3-O-azidosulphate glucofuranose derivatives. 1H-n.m.r. spectra and infrared spectra were used