Synthesis of steroidal cyclophosphamides.
The Reformatsky product of estrone methyl ether and ethyl bromo-acetate was transformed by two separate routes to 21-amino-3-methoxy-17alpha-pregna-1,3,5(10)-trien-17beta-ol (9). Cyclization with bis- (2-chloroethyl) phosphoramide dichloride produced the steroidal cyclophosphamide 10. Analogous syntheses transformed androstenolone into steroidal cyclophosphamide 20 and androstenedione into steroidal cyclophosphamide 28.
D000735:Androstenedione; D000736:Androstenes; D055598:Chemical Phenomena; D002621:Chemistry; D003520:Cyclophosphamide / Q000031:analogs & derivatives*; D004970:Estrone; D008722:Methods; D011281:Pregnatrienes; D013256:Steroids; D013329:Structure-Activity Relationship
D000736:Androstenes; D011281:Pregnatrienes; D013256:Steroids; D004970:Estrone; D000735:Androstenedione; D003520:Cyclophosphamide