Practical synthesis of fully protected globotriaose and its glycopolymers

Convenient and useful construction of a trisaccharide moiety of globotriaosyl ceramide was performed by means of modified Ogawa’s protocol. In order to evaluate an efficiency of new class of glycopolymers, further chemical transformations of the trisaccharide were accomplished to afford a globotriaosyl carbohydrate monomer, and homopolymerization of the monomer by a general radical polymerization protocol gave a high-density glycopolymer in 84.3% yield after usual work-up procedures. In addition to the homopolymer, a copolymer composed of carbohydrate units and acrylamide units was also synthesized by the radical polymerization in 96.7% yield.