Reaction of isocyanatosulphonyl chloride with unsaturated sugars. The preparation of 3-amino-3-dexoy-D-glucal-derivatives

Abstract

Isocyanatosulphonyl chloride (3) reacts with tri-O-acetyl-D-glucal in ether to give 1,3,4,6-tetra-O-acetyl-2-C-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex- 2-enopyranosyl)-2-deoxy-β-D-glucoyranose (1), and with ethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (2) to give an unstable product which can be reduced to 4,6-di-O-acetyl-3-deoxy-3-(ethoxycarbonylamino)-D-glucal (4).