20535-16-4

Basic information

• Product Name: 9-(3'-fluoro-3'-deoxyxylofuranosyl)adenine
• Synonyms: 9-(3'-fluoro-3'-deoxyxylofuranosyl)adenine;3'-Deoxy-3'-fluoro-xyloadenosine
• CAS NO: 20535-16-4
• Molecular Formula: C₁₀H₁₂FN₅O₃
• Molecular Weight: 285.2317832
• Mol File: 20535-16-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 628.6±65.0 °C(Predicted)
• Appearance: /
• Density: 2.01±0.1 g/cm3(Predicted)
• PKA: 12.45±0.70(Predicted)
• CAS DataBase Reference: 9-(3'-fluoro-3'-deoxyxylofuranosyl)adenine(CAS DataBase Reference)
• NIST Chemistry Reference: 9-(3'-fluoro-3'-deoxyxylofuranosyl)adenine(20535-16-4)
• EPA Substance Registry System: 9-(3'-fluoro-3'-deoxyxylofuranosyl)adenine(20535-16-4)

Safety Data

• Hazardous Substances Data: 20535-16-4(Hazardous Substances Data)

Upstream product

• 2627-64-7 9-(2,3-anhydro-β-D-ribofuranosyl)adenine 

Downstream Products

• 132849-69-5 N-(9-((2R,3S,4R,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide 
• 110143-06-1 9-[5-O-(monomethoxytrityl)-3-fluoro-3-deoxy-β-D-xylo-pentofuranosyl]adenine 
• 168918-57-8 C₃₈H₂₈FN₅O₇ 
• 484024-77-3 9-[5-O-(tert-butyldimethylsilyl)-3-deoxy-3-fluoro-2-O-(phenoxythiocarbonyl)-β-D-xylofuranosyl]adenine 
• 132849-70-8 N⁶-Benzoyl-9-<3'-deoxy-3'-fluoro-5'-O-(monomethoxytrityl)-β-D-xylofuranosyl>adenine 
• 168918-60-3 9-<2-O-Benzoyl-3-fluoro-3-deoxy-5-O-(monomethoxytrityl)-β-D-xylofuranosyl>-N⁶,N⁶-dibenzoyladenine 
• 168918-64-7 9-<3-Fluoro-3-deoxy-5-O-(monomethoxytrityl)-β-D-xylofuranosyl>-N⁶-benzoyladenine 2'-<2-chlorophenyl 2-(4-nitrophenyl)ethyl phosphate> 
• 168918-62-5 9-(2-O-Benzoyl-3-fluoro-3-deoxy-β-D-xylofuranosyl)-N⁶,N⁶-dibenzoyladenine 
• 110143-07-2 9-[5-O-(monomethoxytrityl)-3-fluoro-3-deoxy-2-O-(phenyoxythiocarbonyl)-β-D-xylo-pentofuranosyl]adenine 
• 110143-09-4 9-(3-fluoro-2,3-dideoxy-β-D-threo-pentofuranosyl)adenine 
• 110143-08-3 9-{(2R,4R,5R)-4-Fluoro-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-ylamine 
• 132849-71-9 N⁶-Benzoyl-9-<2'-O-<(tert-butyl)dimethylsilyl>-3'-deoxy-3'-fluoro-β-D-xylofuranosyl>adenine 

Relevant articles and documents

Role of the stereochemistry of 3'-fluoro-3'-deoxy analogues of 2-5A in binding to and activation of mouse RNase L

The synthesis of two sets of analogues of 2-5A trimer containing 9-(3-fluoro-3-deoxy-β-D-xylo-furanosyl)adenine (AF) or 3'-fluoro-3'-deoxyadenosine (AF) at different positions of the chain is described, along with the preparation of the corresponding 5'-monophosphates and 5'-diphosphorylated (core) trimers.The ability of each ribo and xylo isomeric pair of fluorodeoxy analogues of 2-5A (i) to compete with p3(A2'p)3A3'pC3'p for binding to RNase L in L929 cell extracts, and (ii) to activate the partially purified RNase L from L929 cell extracts to hydrolyze poly(U), was compared to that of the related 3'-deoxy analogue and the parent trimer, p3A3, using radiobinding and RNase L-(2',5')pentaadenylate(core)-agarose assays, respectively.Evidence is presented to show that the stereochemistry of the trimers plays an important role, specifically in the second process.The most striking observation is that, compared to 2-5A, p3A(AF)A was found to be nine times more effective an activator of RNase L, whereas isomeric p3A(AF)A is 30 times less effective.