title: Nucleosides and nucleotides. 232. Synthesis of 2'-C-methyl-4'-thiocytidine: unexpected anomerization of the 2'-keto-4'-thionucleoside precursor.
abstract: The synthesis of 2'-C-methyl-4'-thiocytidine (16) is described. Since the 2'-keto-4'-thiocytidine derivative 2beta unexpectedly isomerized to 2alpha and the methylation of 2beta proceeded predominantly from the less hindered alpha-face to give 7, the desired product 16 was synthesized via the Pummerer reaction of the sulfoxide 14 and N4-benzoylcytosine.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita-ku, Sapporo, Japan.
authors.forename: Daisuke
authors.initials: D
authors.lastname: Kaga
authors.forename: Noriaki
authors.initials: N
authors.lastname: Minakawa
authors.forename: Akira
authors.initials: A
authors.lastname: Matsuda
mesh_terms: D003562:Cytidine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D003562:Cytidine