F. Iglesiasguerra et al., ALKYLATING-AGENTS FROM SUGARS - CYCLOPHOSPHAMIDES DERIVED FROM 2-AMINO-2-DEOXY-D-ALLOSE, Carbohydrate research, 308(1-2), 1998, pp. 57-62
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.