Alkylating agents from sugars. Cyclophosphamides derived from 2-amino-2-deoxy-d-allose

Cyclophosphamides derived from alkyl 2-amino-4,6-O-benzylidene-2-deoxy-β-d-allopyranosides have been synthesized with good yield by treatment of the corresponding 2-amino-2-deoxy-d-allose derivatives with bis(2-chloroethyl)phosphoramide dichloride. The ring-forming reaction took place with very high diastereoselectivity. Subsequent hydrogenolysis gave excellent yields of cyclophosphamides derived from alkyl 2-amino-2-deoxy-β-d-allopyranosides, with hydrophilicity greater than that of the precursors. The starting material was easily available from 2-acetamido-2-deoxy-d-glucose.