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

Abstract

A new class of organoselenium-saccharide derivatives, 2-amino-2-deoxy-β-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.

Keywords:

• Benzoisoselenazolone
• organoselenium-saccharide derivatives
• reaction mechanism

ACKNOWLEDGMENT

This work was financially supported by the Key International Cooperation Project of the Chinese Ministry of Science and Technology (Grant No. 2008DFA31040).