Download PDF
Synthesis 1997; 1997(2): 225-228
DOI: 10.1055/s-1997-1170
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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

      >