Synthesis of novel D-2'-deoxy-2'-C-difluoromethylene-4'-thiocytidine as a potential antitumor agent.
[reaction: see text] 2'-Deoxy-2'-C-difluoromethylene-4'-thiocytidine (4) as a potential antitumor agent was synthesized starting from L-xylose via 2-deoxy-2-C-difluoromethylene-4-thiosugar as a key intermediate. An elimination product, 8, was always formed as the major product during removal of the protecting groups under acidic or basic conditions. However, utilizing neutral reaction conditions to remove the protecting groups afforded the desired product 4 exclusively.
Lim
Moo Hong
MH
College of Pharmacy and Division of Chemistry and Molecular Engineering, Seoul National University, Seoul 151-742, Korea.
Kim
Hea Ok
HO
Moon
Hyung Ryong
HR
Chun
Moon Woo
MW
Jeong
Lak Shin
LS
D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D003841:Deoxycytidine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D006801:Humans; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D014407:Tumor Cells, Cultured
C451482:2'-deoxy-2'-C-difluoromethylene-4'-thiocytidine; D000970:Antineoplastic Agents; D007202:Indicators and Reagents; D003841:Deoxycytidine