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Nucleosides and nucleotides. 232. Synthesis of 2'-C-methyl-4'-thiocytidine: unexpected anomerization of the 2'-keto-4'-thionucleoside precursor.
- Source :
-
Nucleosides, nucleotides & nucleic acids [Nucleosides Nucleotides Nucleic Acids] 2005; Vol. 24 (10-12), pp. 1789-800. - Publication Year :
- 2005
-
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.
- Subjects :
- Cytidine analogs & derivatives
Cytidine chemistry
Cytidine chemical synthesis
Subjects
Details
- Language :
- English
- ISSN :
- 1525-7770
- Volume :
- 24
- Issue :
- 10-12
- Database :
- MEDLINE
- Journal :
- Nucleosides, nucleotides & nucleic acids
- Publication Type :
- Academic Journal
- Accession number :
- 16438048
- Full Text :
- https://doi.org/10.1080/15257770500267204