ALKYLATING-AGENTS FROM SUGARS - CYCLOPHOSPHAMIDES DERIVED FROM 2-AMINO-2-DEOXY-D-ALLOSE

Cyclophosphamides derived from alkyl o-4,6-O-benzylidene-2-deoxy-beta- D-allopyranosides sides have been synthesized with good yield by treat ment of the corresponding 2-amino-2-deoxy-D-allose derivatives with bi s(2-chloroethyl)phosphoramide dichloride. The ring-forming reaction to ok place with very high diastereoselectivity. Subsequent hydrogenolysi s gave excellent yields of cyclophosphamides derived from alkyl 2-amin o-2-deoxy-beta-D-allopyranosides, with hydrophilicity greater than tha t of the precursors. The starting material was easily available from 2 -acetamido-2-deoxy-D-glucose. (C) 1998 Elsevier Science Ltd. All right s reserved.