- Copper-mediated arylsulfanylations and arylselanylations of pyrimidine or 7-deazapurine nucleosides and nucleotides
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The syntheses of 5-arylsulfanyl- or 5-arylselanylpyrimidine and 7-arylsulfanyl- or 7-arylselanyl-7-deazapurine nucleosides and nucleotides were developed by the Cu-mediated sulfanylations or selanylations of the corresponding 5-iodopyrimidine or 7-iodo-7-
- Botha, Filip,Slaví?ková, Michaela,Pohl, Radek,Hocek, Michal
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- Facile photocyclization chemistry of 5-phenylthio-2′-deoxyuridine in duplex DNA
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We report here the synthesis of 5-phenylthio-2′-deoxyuridine (d PhSU), its incorporation into oligodeoxynucleotides (ODNs), and its photocyclization chemistry. Irradiation of dinucleoside monophosphate d( PhSUG) and dPhSU-
- Zeng, Yu,Cao, Huachuan,Wang, Yinsheng
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p. 2527 - 2530
(2007/10/03)
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- Synthesis of 5-arylthiouridines via electrophilic substitution of 5- bromouridines with diaryl disulfides
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Novel synthetic method of 5-arylthiouridine derivatives is described. Treatment of 5-bromo-2',3'-O-isopropylideneuridine (1a) with diaryl disulfides in the presence of sodium hydride at ambient temperature gave the 5-arylthiouridines (2) in moderate yields. The present method is devised by virtue of a combination of efficient participation of the 5'-hydroxy group onto the uracil ring and the electrophilic nature of diaryl disulfide, which was applied to the synthesis of 5-arylthio-1-β-D-arabinofuranosyluracils (8).
- Hirota, Kosaku,Tomishi, Tetsuo,Maki, Yoshifumi,Sajiki, Hironao
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p. 161 - 173
(2007/10/03)
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- Palladium-Mediated Synthesis of C-5 Pyrimidine Nucleoside Thioethers from Disulfides and Mercurinucleosides
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Thioether-linked side chains can be created at C-5 of pyrimidine nucleosides via a palladium-mediated reaction of mercurated nucleosides with organic disulfides. 5-(Chloromercuri)-2'-deoxyuridine reacts with butyl disulfide, phenyl disulfide, dimethyl 3,3'-dithiopropionate, and N,N'-bis(trifluoroacetyl)cystamine to yield respectively 5-(1-thiapentyl)-2'-deoxyuridine, 5-(phenylthio)-2'-deoxyuridine, 5--2'-deoxyuridine, and 5--2'-deoxyuridine in yields ranging from 46 to 73percent.Other mercurated nucleosides, including 5-(chloromercuri)-2'-deoxycytidine, 5-(chloromercuri)cytidine, and 5-(chloromercuri)tubercidin react with N,N'-bis(trifluoroacetyl)cystamine and lithium-palladium chloride in methanol to yield the corresponding coupled products, but the yields are much lower (5-10percent).The nucleoside coupling reaction is complicated by competing side reactions between disulfides and Pd2+, which remain to be elucidated
- Bergstrom, Donald E.,Beal, Peter,Jenson, Jeffrey,Lin, Xiaoping
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p. 5598 - 5602
(2007/10/02)
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