16006-62-5Relevant articles and documents
Synthesis and evaluation of the substrate activity of C-6 substituted purine ribosides with E. coli purine nucleoside phosphorylase: Palladium mediated cross-coupling of organozinc halides with 6-chloropurine nucleosides [1]
Hassan, Abdalla E.A.,Abou-Elkhair, Reham A.I.,Riordan, James M.,Allan, Paula W.,Parker, William B.,Khare, Rashmi,Waud, William R.,Montgomery, John A.,Secrist III, John A.
, p. 167 - 174 (2012)
A series of C-6 alkyl, cycloalkyl, and aryl-9-(β-d-ribofuranosyl) purines were synthesized and their substrate activities with Escherichia coli purine nucleoside phosphorylase (E. coli PNP) were evaluated. (Ph 3P)4Pd-mediated cross-c
Reaction of 6-Methylsulfonylpurine Riboside with Carbon Nucleophiles and the Synthesis of 6-Alkylpurine Nucleosides. (Nucleosides and Nucleotides. XXIX)
Yamane, Akira,Matsuda, Akira,Ueda, Tohru
, p. 150 - 156 (2007/10/02)
Treatment of 6-methylsulfonyl-9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)purine with ethyl acetoacetate and sodium hydride in tetrahydrofuran afforded, after deblocking, 6-ethoxycarbonylmethyl-9-β-D-ribofuranosylpurine.Similarly, replacement of the 6-methylsulfonyl moiety with other carbanions derived from diethyl malonate, ethyl cyanoacetate, malononitrile, nitromethane, and sodium cyanide gave the corresponding 6-C-substituted purine nucleosides.Most of these derivatives exist as the 6-(1H)-exomethylene tautomeric forms. 6-Ethoxycarbonylmethylpurine riboside was further converted to 6-methyl, ethyl, propyl, butyl, and pentyl-purine ribosides by decarboxylation or prior alkylation of the methylene group followed by de-carboxylation.This reaction sequence facilitated the preparation of hitherto almost inaccessible alkyl or C-substituted purine nucleosides.Keywords- nucleophilic aromatic substitution; carbon nucleophiles; purine nucleosides; UV; NMR; tautomerism