Synthesis and absolute configuration assignments of enantiomeric forms of ifosphamide, sulfosphamide, and trofosphamide

K Pankiewicz, R Kinas, WJ Stec, AB Foster…

Index: Pankiewicz,K. et al. Journal of the American Chemical Society, 1979 , vol. 101, p. 7712 - 7718

Full Text: HTML

Citation Number: 42

Abstract

Abstract: Using N-(S)-a-or N-(R)-a-methylbenzyl-3-aminopropan-l-ol as the starting material, the diastereomers of 2-chloro-3-[(S)-a-or (R)-a-methylbenzyl] tetrahydro-2H-l, 3, 2- oxazaphosphorine 2-oxide were obtained in the ratio 80: 20. Their conversion via P- aziridines (14) into 2-chloroethylamino derivatives (15) and separation of the latter into diastereometrically pure forms allowed the further synthesis of enantiomers of ...