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

• Published in: Synthesis (Stuttgart) no. 2; pp. 225 - 229
• Main Authors: Serafinowski, PJ, Barnes, CL
• Format: Journal Article
• Language: English
• 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

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�...