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Synthesis 1997; 1997(2): 225-228
DOI: 10.1055/s-1997-1170
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Synthesis of 3'-Difluoromethylene-3'-deoxythymidine and Some Derivatives

Pawel J. Serafinowski* , Colin L. Barnes
  • *CRC Centre for Cancer Therapeutics at the Institute of Cancer Research, 15 Cotswold Road, Sutton, Surrey, SM2 5NG, UK, Fax +44(181)7707899; E-mail p.serafinowski@icr.ac.uk
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Publication Date:
31 December 2000 (online)

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Ultrasound-assisted reaction of the 3'-oxo derivative of thymidine (1) with bromodifluoromethyl[tris(dimethylamino)phosphonium] bromide (8) and zinc, gives the corresponding 3'-difluoromethylene nucleoside 5. Subsequent removal of the dimethoxytrityl group provides hitherto unreported 3'-difluoromethylene-3'-deoxythymidine (6), a new analogue of AZT.

3'-oxothymidine - difluoromethylenation - difluoromethyl phenylsulfone - Sml2 elimination - detritylation