CHEMICAL SYNTHESIS OF POLYSACCHARIDES .1. DEVELOPMENT OF METHOD AND SYNTHESIS OF GENTIODEXTRINS

Method have been developed for the specific synthesis of oligosaccharides by using partially acetylated derivatives of d-glucose. When 1,2,3,4-tetra-O-acetyl-β-d-glucopyranose was fused with a catalytic amount of toluene-p-sulphonic acid, 1,6-anhydro-β-d-glucopyranose, gentiobiose, gentiotriose, and gentiotetraose were the major sugars recovered following de-acetylation of the reaction mixture. With zinc chloride as catalyst under more forcing conditions, larger proportions of gentiodextrins, some of which were of the polysaccharide type, were formed. Two polysaccharide preparations have been examined and shown to be mainly composed of β-(1→6)-linked d-glucopyranose residues. © 1969.