Reaction of ammonia with acylated aldoheptoses : Derivatives of D- glycero- D- gulo-heptose, D-glycero- L- manno-heptose, and D- glycero- D- galacto-heptose

Abstract

The reaction of methanolic ammonia with the hexa- O-acetyl and hexa- O-benzoyl derivatives of D- glycero- D- gulo-heptose, D- glycero- L- manno-heptose, and D- glycero- D- galacto-heptose affords the 1,1-bis(acylamido)-1-deoxy- D-heptitols (2,3), from which the acetates have been prepared. The yields of 2 and 3 are in general higher than those of the corresponding hexose derivatives. On ammonolysis of hexa- O-benzoyl- D- glycero- L- manno-heptose, an N-benzoyl- D- glycero- L- manno-heptosylamine is formed, together with the main product.