132722-95-3

Basic information

• Product Name: 6-Chloro-9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)-9H-purine
• Synonyms: 6-Chloro-9-(2,3-dideoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purine;6-Chloro-9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)-9H-purine
• CAS NO: 132722-95-3
• Molecular Formula: C₁₀H₁₀ClFN₄O₂
• Molecular Weight: 272.66
• Mol File: 132722-95-3.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-Chloro-9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)-9H-purine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Chloro-9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)-9H-purine(132722-95-3)
• EPA Substance Registry System: 6-Chloro-9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)-9H-purine(132722-95-3)

Safety Data

• Hazardous Substances Data: 132722-95-3(Hazardous Substances Data)

Upstream product

• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 

Downstream Products

• 117525-25-4 9-[2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl]-1,6-dihydro-6-oxo-9H-purine 
• 110143-10-7 iodenosine 

Relevant articles and documents

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.