160533-28-8Relevant articles and documents
SYNTHESIS OF DEOXY, DIDEOXY AND DIDEHHYDRODIDEOXY ANALOGS OF 9-(4-C-HYDROXYMETHYL-&α-L-PENTOFURANOSYL)ADENINE
Hrebabecky, Hubert,Holy, Antonin
, p. 1654 - 1664 (2007/10/02)
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.
Novel 4'-branched nucleosides
Surzhykov,Krayevsky
, p. 2283 - 2305 (2007/10/02)
Total chemical synthesis of 4'-hydroxymethylnucleosides with an additional modification in a sugar residue was developed. The synthesis was made by condensation of corresponding protected sugars and nucleic bases with subsequent deprotection. In such a wa