521060-16-2

Upstream product

• 108-24-7 acetic anhydride 
• 476209-84-4 (2S,4S)-(+)-4-tert-butyldiphenylsilyloxymethyl-2-fluoro-γ-butyrolactone 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 102717-30-6 (3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-dihydro-furan-2-one 
• 102717-29-3 (5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 

Downstream Products

• 136228-17-6 9-[5-(tert-butyl-diphenyl-silanyloxymethyl)-3-fluoro-tetrahydro-furan-2-yl]-6-chloro-9H-purine 
• 521060-17-3 ((2S,4S,5R)-5-Bromo-4-fluoro-tetrahydro-furan-2-ylmethoxy)-tert-butyl-diphenyl-silane 

Relevant academic research and scientific papers

A concise synthesis of anti-viral agent F-ddA, starting from (S)-dihydro-5-(hydroxymethyl)-2(3H)-furanone

Anti-HIV agent β-F-ddA (1) has been synthesized starting from readily available non-sugar, (S)-(+)-Dihydro-5-(hydroxymethyl)-2-(3H)-furanone (4). A highly syn-stereoselective fluorination of the hydroxy lactone 2 generates the key intermediate fluorolactone 5 in a short and concise synthetic sequence. Reduction of 5 followed by bromination generates the aglycon which is glycosylated to generate F-ddA by amination and deprotection. Steric bulk of the 5-protecting group has minimal effect on the steric course of glycosylation.