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Stereospecific synthesis of tetradeuterated (R)‐ and (S)‐ifosfamide
Author(s) -
Wang Jeff J.H.,
Chan Kenneth K.
Publication year - 1996
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(199602)38:2<105::aid-jlcr821>3.0.co;2-x
Subject(s) - ifosfamide , chemistry , stereoselectivity , stereospecificity , yield (engineering) , enantiomer , stereochemistry , combinatorial chemistry , organic chemistry , chemotherapy , catalysis , medicine , materials science , etoposide , metallurgy
The tetradeuterated analogues of (R)‐ and (S)‐ifosfamide [(S)‐ and (R)‐2‐(2‐chloro‐2,2‐dideuterioethyl)amino‐3‐(2‐chloroethyl)‐6,6‐dideuterio‐tetrahydro‐2H‐ 1,3,2 ‐oxazaphosphorin‐2‐oxide, (S)‐ and (R)‐1‐d 4 ] were synthesized by modification of a literature procedure. The enantiomers of α‐methylbenzylamine were employed as the resolving agents in the multi‐step synthesis in a 9% overall yield. The selected labeled positions should minimize potential isotope effects useful for the investigation of stereoselective metabolism of ifosfamide by pseudoracemate methodology.