1969
DOI: 10.1135/cccc19692316
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Nucleic acid components and their analogues. CXXVII. Synthesis of uridine and cytidine 6-methyl and 5,6-dimethyl derivatives

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Cited by 23 publications
(9 citation statements)
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“…Cytidine residues in nucleic acids are usually more reactive than their uridine or thymidine counterparts 26. Cytidine N ‐oxide derivatives are obtained by oxidation of the natural nucleoside or nucleotide with different stoichiometric oxidants including m ‐CPBA,27 terephthalic acid,28 and hydrogen peroxide (H 2 O 2 ) 29. To the best of our knowledge the oxidation with MTO is the first of the reported catalytic procedures so far described for the synthesis of these derivatives.…”
Section: Resultsmentioning
confidence: 99%
“…Cytidine residues in nucleic acids are usually more reactive than their uridine or thymidine counterparts 26. Cytidine N ‐oxide derivatives are obtained by oxidation of the natural nucleoside or nucleotide with different stoichiometric oxidants including m ‐CPBA,27 terephthalic acid,28 and hydrogen peroxide (H 2 O 2 ) 29. To the best of our knowledge the oxidation with MTO is the first of the reported catalytic procedures so far described for the synthesis of these derivatives.…”
Section: Resultsmentioning
confidence: 99%
“…The less polar nucleoside 8 was eluted with n-hexane-ethyl acetate (1:1) and crystallized (ethanol) giving The Ni-nucleoside 7 was eluted with ethyl acetate. Crystallization (CH2Cl2-pentane) gave 5.77 g (65.9%) of 7 in needles: mp 176-178°; [«]20d -10.3°(c 1, CHCI3); nmr (CDC13) 5.81 (d, 1, J < 1 Hz, H-T), 2.29 (s, 3, 6-CH3), 1.99 The analogous reaction in 1,2-dichloroethane (addition of SnCLj at 0°, then 6 hr at 22°) gave 60.3% 8 and 10.3% 7.…”
Section: Methodsmentioning
confidence: 99%
“…The filtrate was dried and evaporated to leave 2.7 g of residue which was chromatographed on 60 g of silica gel with benzene, followed by benzene-ether (1:1, v/v). Evaporation of the fractions eluted with benzene and crystallization of the residue from methylene chloride-hexane yielded 1.33 g (49%) of product: mp 122-124°; nmr (CDCls) 2.78 (s,3,NCH3),4,C2 H, C3 H), 4.37 (s, 2, NCH2C«H6), 6.25-6.7 (m, 3, C6 H, C, H, C8 ), 7.21 (s, 5, C"H5).…”
Section: -Benzylmentioning
confidence: 99%