Asymmetric synthesis of enantiomeric cyclophosphamides

…, H Ueda, K Nakagawa, N Bodor

Index: Sato, Tadao; Ueda, Hiraki; Nakagawa, Kazuyuki; Bodor, Nicholas Journal of Organic Chemistry, 1983 , vol. 48, # 1 p. 98 - 101

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Citation Number: 22

Abstract

An efficient asymmetric synthesis of the enantiomers of cyclophosphamide was developed on the basis of three important steps:(1) a highly stereospecific synthesis of the 2-chloro-2- oxo-1, 3, 2-oxazaphosphorinane ring from an optically active amino alcohol and phosphoryl chloride (diastereomer ratio obtained is 101 to 12: l);(2) the use of the diethanolamine derivative tu an intermediate for introduction of the mustard group;(3) a novel, simple, and ...