K. Tsujihara, H. Kurita, K. Mitsutaka
Jun 1, 1977
Citations
0
Influential Citations
36
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
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 ...