Alkylating agents from sugars: Synthesis of chlorambucil derivatives carried by chiral glycosyl glycerols derived from<scp>D</scp>-Glucosamine

Chlorambucilamide derivatives involving chiral glycosyl glycerols derived from D-glucosamine were synthesized in good yield by coupling the chlorambucil moiety to the amino group of ω-amino-(ω-1)-hydroxyalkyl 2-acylamino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosides, and subsequent hydrolysis of the benzylidene group. The starting material was easily available from 2-acetamido-2-deoxy-D-glucose. The bonding of 2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosylamine to chlorambucil by formation of an amide function is also described. Chirality Chirality 14:199–203, 2002. &#169; 2002 Wiley-Liss, Inc.