Synthesis of 3′-fluoromethylthio-, 3′-fluoromethylsulfinyl- and 3′-fluoromethylsulfonyl-substituted 3′-deoxythymidine

Abstract

3′- Deoxy- 3′-(fluoromethylthio)thymidine 2 is synthesized from 5′-O-benzoyl-3′-deoxy-3′-(methylsulfinyl)thymidine 9 by using DAST. 5′-O- Benzoyl-3′-deoxy-3′-(fluoromethylthio)thymidine is used as starting material for the synthesis of the sulfoxide 3 and the sulfone 4. Both sulfoxides 3A and 3B show a C3′-endo sugar conformation.