Alkylating agents from sugars: synthesis of chlorambucil derivatives carried by chiral glycosyl glycerols derived from D-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 omega-amino-(omega-1)-hydroxyalkyl 2-acylamino-4,6-O-benzylidene-2-deoxy-beta-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-beta-D-galactopyranosylamine to chlorambucil by formation of an amide function is also described.
Iglesias-Guerra
Fernando
F
Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad de Sevilla, Sevilla, Spain. iglesias@fafar.us.es
Candela
José I
JI
Blanco
Eugenia
E
Alcudia
Felipe
F
Vega-Pérez
José M
JM
D000477:Alkylating Agents / Q000138:chemical synthesis*; D002241:Carbohydrates / Q000737:chemistry*; D002699:Chlorambucil / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D005944:Glucosamine / Q000737:chemistry*; D005990:Glycerol / Q000737:chemistry*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D012997:Solvents; D013237:Stereoisomerism
D000477:Alkylating Agents; D002241:Carbohydrates; D007202:Indicators and Reagents; D012997:Solvents; D002699:Chlorambucil; D005944:Glucosamine; D005990:Glycerol