160533-31-3

Basic information

• Product Name: 9-(2,5-di-O-acetyl-4-C-acetoxymethyl-3-O-methanesulfonyl-α-L-arabinofuranosyl)-N⁶-benzoyladenine
• CAS NO: 160533-31-3
• Molecular Weight: 605.582
• Mol File: 160533-31-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 9-(2,5-di-O-acetyl-4-C-acetoxymethyl-3-O-methanesulfonyl-α-L-arabinofuranosyl)-N⁶-benzoyladenine(CAS DataBase Reference)
• NIST Chemistry Reference: 9-(2,5-di-O-acetyl-4-C-acetoxymethyl-3-O-methanesulfonyl-α-L-arabinofuranosyl)-N⁶-benzoyladenine(160533-31-3)
• EPA Substance Registry System: 9-(2,5-di-O-acetyl-4-C-acetoxymethyl-3-O-methanesulfonyl-α-L-arabinofuranosyl)-N⁶-benzoyladenine(160533-31-3)

Safety Data

• Hazardous Substances Data: 160533-31-3(Hazardous Substances Data)

Upstream product

• 68024-03-3 (3aR,6R,6aR)-2,2-Dimethyl-5,5-bis-trityloxymethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol 
• 55797-64-3 1,2-O-isopropylidene-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose 
• 4005-49-6 N-benzoyladenine 

Relevant articles and documents

SYNTHESIS OF DEOXY, DIDEOXY AND DIDEHHYDRODIDEOXY ANALOGS OF 9-(4-C-HYDROXYMETHYL-&α-L-PENTOFURANOSYL)ADENINE

Condensation of 1,2-di-O-acetyl-3,5-di-O-benzoyl-4-C-benzoyloxymethyl-L-arabinofuranose with N6-benzoyladenine, catalyzed with tin tetrachloride, afforded nucleoside I, which upon partial deacetylation and subsequent mesylation was converted into 9-(3,5-di-O-benzoyl-4-C-benzoyloxymethyl-2-O-methanesulfonyl-α-L-arabinofuranosyl)adenine (III). 9-(2,5,6-Tri-O-acetyl-4-C-acetoxymethyl-3-O-methanesulfonyl-α-L-arabinofuranosyl)-N6-benzoyladenine (V) was obtained by condensation of 1,2,5-tri-O-acetyl-4-C-acetoxymethyl-3-O-methanesulfonyl-L-arabinose with N6-benzoyladenine.Reaction of mesyl derivatives III and IV with methanolic sodium methoxide afforded 2',3'-anhydro nucleosides VIa and VIIa, which were acetylated to give 9-(5-O-acetyl-4-C-acetoxymethyl-2,3-anhydro-α-L-ribofuranosyl)adenine (VIb) and 9-(5-O-acetyl-4-C-acetoxymethyl-2,3-anhydro-α-L-lyxofuranosyl)adenine (VIIb).Epoxy derivative VIb was cleaved with bromotrimethylsilane to 9-(5-O-acetyl-4-C-acetoxymethyl-2-bromo-2-deoxy-α-L-arabinofuranosyl)adenine (VIIIa); the same reaction with epoxy derivative VIIb afforded a mixture of 9-(5-O-acetyl-4-C-acetoxymethyl-2-bromo-2-deoxy-α-L-xylofuranosyl)adenine (IXa) and 9-(5-O-acetyl-4-C-acetoxymethyl-3-bromo-3-deoxy-α-L-arabinofuranosyl)adenine (Xa).Their dehalogenation with tributylstannane and subsequent deacetylation led to 2-deoxy-4-C-acetoxymethyl-α-L-erythro-pentofuranosyl)adenine (VIIIc), 9-(2-deoxy-4-C-hydroxymethyl-α-L-threo-pentofuranosyl)adenine (IXc) and 9-(3-deoxy-4-C-hydroxymethyl-α-L-threo-pentofuranosyl)adenine (Xc). 9-(2,5-Di-O-acetyl-4-C-acetoxymethyl-2-bromo-2-deoxy-α-L-arabinofuranosyl)adenine (VIIId), prepared by acetylation of VIIIa, on reductive elimination with Cu/Zn couple and subsequent deacetylation afforded 9-(2,3-dideoxy-4-C-hydroxymethyl-α-L-glycero-pent-2-enofuranosyl)adenine (XIb). 9-(2,3-Dideoxy-4-C-hydroxymethyl-α-L-glycero-pentofuranosyl)-adenine (XIIb) was obtained either by catalytic hydrogenation of bromo derivative VIIId, followed by deacetylation, or by catalytic hydrogenation of didehhydro derivative XIb.The nucleosides synthesized were tested for antiviral activity.