Nucleosides and nucleotides. 232. Synthesis of 2'-C-methyl-4'-thiocytidine: unexpected anomerization of the 2'-keto-4'-thionucleoside precursor.
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.
Kaga
Daisuke
D
Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita-ku, Sapporo, Japan.
Minakawa
Noriaki
N
Matsuda
Akira
A
D003562:Cytidine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry
D003562:Cytidine