217658-58-7

Upstream product

• 208249-85-8 (E)-(R)-6-Benzyloxy-3-benzyloxymethyl-3-fluoro-hex-4-enoic acid ethyl ester 
• 208249-84-7 (E)-(S)-1,5-Bis-benzyloxy-4-fluoro-pent-3-en-2-ol 
• 208249-86-9 (S)-4-Benzyloxy-3-fluoro-3-formyl-butyric acid ethyl ester 
• 100-39-0 benzyl bromide 
• 120633-60-5 (2S)-2-hydroxy-2-(benzyloxymethyl)-4-penten-1-ol 
• 217658-49-6 (2S)-2-fluoro-2-(benzyloxymethyl)-4-penten-1-yl benzoate 
• 217658-45-2 (2R)-2-hydroxy-2-(benzyloxymethyl)-4-penten-1-yl benzoate 
• 217658-51-0 (2R)-2-fluoro-2-(benzyloxymethyl)-4-penten-1-ol 
• 108-24-7 acetic anhydride 

Downstream Products

• 217659-28-4 (+)-1-(3'-O-benzyl-2,3-dideoxy-3-fluoroapio-α-L-furanosyl)thymine 
• 217659-24-0 (+)-1-(3'-O-benzyl-2,3-dideoxy-3-fluoroapio-β-L-furanosyl)thymine 
• 217658-71-4 (+)-N⁴-acetyl-1-(3'-O-benzyl-2,3-dideoxy-3-fluoroapio-α-L-furanosyl)cytosine 
• 217658-67-8 (-)-N⁴-acetyl-1-(3'-O-benzyl-2,3-dideoxy-3-fluoroapio-β-L-furanosyl)cytosine 

Relevant academic research and scientific papers

Asymmetric synthesis of 2′,3′-dideoxy-3′- fluoroapiofuranosyl nucleosides

An efficient stereoselective synthetic method for each stereoisomer of enantiomerically pure 2′,3′-dideoxy-3′-fluoroapiofuranosyl nucleosides was developed. The key features of this strategy are the enantiospecific fluorination of the tert-alcohol and the

Enantiomeric synthesis of 3′-fluoro-apionucleosides using Claisen rearrangement

Enantiomeric synthesis of 3′-fluoro-apionucleosides was accomplished from 1,2-O-isopropylidene D-glyceraldehyde. The key intermediate, γ,δ-unsaturated tert-fluoro ethyl ester 7 from the fluoro allylic alcohol derivative 5 was achieved via Claisen rearrangement reaction with a 90.4% enantioselectivity. The condensation of the intermediate 10 with silylated N4-benzoylcytosine and 6-chloropurine followed by deprotection gave the desired pyrimidine and purine apionucleosides, respectively.