100634-97-7Relevant articles and documents
Copper-mediated arylsulfanylations and arylselanylations of pyrimidine or 7-deazapurine nucleosides and nucleotides
Botha, Filip,Slaví?ková, Michaela,Pohl, Radek,Hocek, Michal
, p. 10018 - 10022 (2016)
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-
Facile photocyclization chemistry of 5-phenylthio-2′-deoxyuridine in duplex DNA
Zeng, Yu,Cao, Huachuan,Wang, Yinsheng
, p. 2527 - 2530 (2007/10/03)
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-
Palladium-Mediated Synthesis of C-5 Pyrimidine Nucleoside Thioethers from Disulfides and Mercurinucleosides
Bergstrom, Donald E.,Beal, Peter,Jenson, Jeffrey,Lin, Xiaoping
, p. 5598 - 5602 (2007/10/02)
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