Stereospecific synthesis of tetradeuterated (R)- and (S)-ifosfamide

✍ Scribed by Jeff J.-H. Wang; Kenneth K. Chan

• Publisher: John Wiley and Sons
• Year: 1996
• Tongue: French
• Weight: 554 KB
• Volume: 38
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/(sici)1099-1344(199602)38:2<105::aid-jlcr821>3.0.co;2-x

✦ Synopsis

The tetradeuterated analogues of (R)and (S)-ifosfamide [(S)and (R)-2-(2-chloro-2,2-

d i d e u t e ~o e t h y l ) a m i n o -3 -( 2 -c h l o r o e t h y l > 6 -

de, (S)-and (Rbl-ddl were synthesized by modification of a literature procedure. The enantiomers of a-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.