Synthesis of 3'-difluoromethylene-3'-deoxythymidine and some derivatives

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�...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 2; pp. 225 - 229
Main Authors Serafinowski, PJ, Barnes, CL
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.02.1997
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
3'-oxothymidine
ROUTE
difluoromethyl phenylsulfone
detritylation
NUCLEOSIDES
STABILITY
CARBONYL-COMPOUNDS
difluoromethylenation
Sm1 elimination
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Summary: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.
ISSN:0039-7881
DOI:10.1055/s-1997-1170