125542-17-8

Basic information

• Product Name: 9-[5-O-(tert-butyldimethylsilyl)-2-deoxy-2-fluoro-3-O-(phenoxythiocarbonyl)-β-D-arabinofuranosyl]adenine
• Synonyms: 9-[5-O-(tert-butyldimethylsilyl)-2-deoxy-2-fluoro-3-O-(phenoxythiocarbonyl)-β-D-arabinofuranosyl]adenine
• CAS NO: 125542-17-8
• Molecular Weight: 519.672
• Mol File: 125542-17-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 9-[5-O-(tert-butyldimethylsilyl)-2-deoxy-2-fluoro-3-O-(phenoxythiocarbonyl)-β-D-arabinofuranosyl]adenine(CAS DataBase Reference)
• NIST Chemistry Reference: 9-[5-O-(tert-butyldimethylsilyl)-2-deoxy-2-fluoro-3-O-(phenoxythiocarbonyl)-β-D-arabinofuranosyl]adenine(125542-17-8)
• EPA Substance Registry System: 9-[5-O-(tert-butyldimethylsilyl)-2-deoxy-2-fluoro-3-O-(phenoxythiocarbonyl)-β-D-arabinofuranosyl]adenine(125542-17-8)

Safety Data

• Hazardous Substances Data: 125542-17-8(Hazardous Substances Data)

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 109304-00-9 6-chloro-9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purine 
• 84025-00-3 1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranose 
• 56632-81-6 1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranosyl bromide 
• 20187-82-0 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine 
• 111727-03-8 6-amino-9-<5-O-(tert-butyldimethylsilyl)-2-deoxy-2-fluoro-β-D-arabinofuranosyl>-9H-purine 
• 1005-56-7 phenylcarbonochloridothioate 

Downstream Products

• 110143-10-7 iodenosine 
• 117525-25-4 2'-F-ara-ddI 

Relevant articles and documents

The beta-fluorine effect. Electronic versus steric effects in radical deoxygenations of fluorine-containing pentofuranose nucleosides.

Stereoselective pyramidalization of free radicals by a vicinal fluorine substituent, the beta-fluorine effect, was invoked to rationalize a 77:23 anti/syn ratio of 2-deuterio-1-fluorocyclopentanes obtained by radical reduction of trans-2-fluoro-1-bromocyclopentane with tributyltin deuteride (Dolbier, W. R., Jr.; Bartberger, M. D. J. Org. Chem. 1995, 60, 4984-4985). We have evaluated analogous reductions of the four possible stereoisomers of some adenine 2'(3')-fluoro-3'(2')-O-phenoxythiocarbonyl nucleoside derivatives. In all cases, the steric effect of adenine on the beta face directs deuterium transfer from the stannane to C2'(C3') on the alpha face of the furanose ring. However, the beta-fluorine effect enhances ratios of deuterium transfer anti to the vicinal fluorine substituent.