Synthesis of D-Glucosamine-Modified Benzo[d][1,2]selenazol-3-(2H)-one Derivatives

A new class of organoselenium-saccharide derivatives, 2-amino-2-deoxy--D-glucose-modified benzo[d][1,2]selenazol-3-(2H)-one derivatives, has been synthesized via the cyclization reaction of 2-(chloroseleno)benzoyl chloride and O-protected D-glucosamine derivatives. An efficient synthetic method for the preparation of this type of compounds was developed. It has been found that acetone can react with the chloroseleno group under basic conditions, and organoselenium-saccharide derivatives with free hydroxy groups were obtained only when the OH-1 group of the saccharide was protected.