Synthesis of 2',3'-dideoxy-2'-trifluoromethylnucleosides from alpha-trifluoromethyl-alpha,beta-unsaturated ester.
The treatment of alpha-bromo-alpha,beta-unsaturated esters 2 with FSO(2)CF(2)CO(2)Me and CuI in DMF/HMPA constitutes a new synthetic scheme for the preparation of alpha-trifluoromethyl-alpha, beta-unsaturated esters 3. The trifluoromethylation of (Z)/(E)-ethyl 3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-bromo-2-propenoate (2e), which is derived from 1-(R)-glyceraldehyde acetonide, yields the key intermediate alpha-trifluoromethyl-alpha,beta-unsaturated esters 3e. This is transformed into anomeric acetates 8a and 8b and is used for the synthesis of a number of 2', 3'-dideoxy-2'-trifluoromethylnucleosides.
Zhang
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Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Qing
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Yu
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D000179:Acrylates / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D000998:Antiviral Agents / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D009705:Nucleosides / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000179:Acrylates; D000970:Antineoplastic Agents; D000998:Antiviral Agents; D009705:Nucleosides