307298-24-4

Upstream product

• 307298-20-0 (2R,4S)-5-(tert-butyldimethylsilyl)-2,3-dideoxy-2-trifluoromethylpentofuranose 
• 307298-18-6 (2R,4S)-5-(tert-butyldimethylsiloxy)-2-trifluoromethylpentan-4-olide 
• 307298-17-5 (2R,4S/2S,4S)-5-hydroxy-2-trifluoromethylpentan-4-olide 
• 402757-16-8 (Z)/(E)-ethyl 3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-trifluoromethyl-2-propenoate 
• 182969-96-6 (Z)/(E)-ethyl 3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-bromo-2-propenoate 
• 26661-13-2 4-N-benzoylcytosine 
• 307298-21-1 (2R,4S)-1-O-acetyl-5-(tert-butyldimethylsilyl)-2,3-dideoxy-2-trifluoromethylpentofuranose 

Relevant academic research and scientific papers

Synthesis of 2′,3′-Dideoxy-2′-trifluoromethylnucleosides from α-Trifluoromethyl-α,β-unsaturated Ester

The treatment of α-bromo-α,β-unsaturated esters 2 with FSO2CF2CO2Me and CuI in DMF/HMPA constitutes a new synthetic scheme for the preparation of α-trifluoromethyl-α,β-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 α-trifluoromethyl-αβ-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.