The Highly Selective Sulfonylation of Cycloheptaamylose and Syntheses of Its Pure Amino Derivatives

Mesitylenesulfonyl chloride reacted selectively with primary hydroxyl groups of cycloheptaamylose to give hexakis (6-O-mesitylsulfonyl)cycloheptaamylose (II) and heptakis(mesitylsulfonyl)cycloheptaamylose (I). The selectivity of mesitylenesulfonyl chloride in the preferential sulfonylation is 24 times larger than that of tosyl chloride. Pure hexakis(6-azido-6-deoxy)cycloheptaamylose (III) and hexakis(6-amino-6-deoxy)cycloheptaamylose (IV) were synthesized from II. Pure heptakis(6-amino-6-deoxy)cycloheptaamylose (VII) and mixture of positional isomers of hexakis(6-amino-6-deoxy)mesitylsulfonylcycloheptaamylose (VIII)* were obtained by the catalytic hydrogenation of the corresponding azido compounds V and VI,* which were themselves given by the reaction of I with sodium azide. These amino derivatives, IV, VII, and VIII,* showed significant antimicrobial activities against such gram-negative bacteria as Escherichia, Shigella, and Pseudomonas. These compounds also exhibited hypocholesterolemic effects in the chick when added in the diet for two weeks, probably through sequestration of intestinal bile acids.