Aminocyclitols. 36. Chlorination and Dechlorination of Aminocyclitol and Inositol Derivatives. Preparation of Dideoxy-and Trideoxystreptamines

Abstract

Abstract Chlorination of four aminocyclitol and six inositol derivatives with sulfuryl chloride gave the chloro substitution products, which were then dechlorinated by hydrogenolysis with Raney nickel or by treatment with tributyltin(IV) hydride giving the corresponding deoxy compounds. Several useful aminocyclitols, including 2,4-dideoxy- and 2,4,5-trideoxystreptamines, were prepared from 2-deoxystreptamine derivatives by these procedures.