title: Synthesis of a North-methanocarba-thymidine (N-MCT) analog.
abstract: A detailed protocol for the synthesis of North-methanocarba-thymidine (N-MCT), a potent antiviral nucleoside with a restricted bicyclo[3.1.0]hexane pseudosugar conformation, is presented. The process is described in two parts. The first basic protocol deals with the synthesis of the carbobicyclic pseudosugar precursor that can be utilized in the syntheses of other bicyclo[3.1.0]hexane nucleosides with natural and non-natural nucleobases. The second basic protocol describes the specific construction of the thymine base in a linear fashion from the carbobicyclic intermediate.
authors.affiliation: J-Star Research, Inc., South Plainfield, New Jersey, USA.
authors.forename: Andrew
authors.initials: A
authors.lastname: Thompson
authors.forename: Victor E
authors.initials: VE
authors.lastname: Marquez
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis / Q000737:chemistry; D054329:Carbasugars / Q000138:chemical synthesis* / Q000737:chemistry; D018258:Herpesvirus 2, Human / Q000187:drug effects; D009690:Nucleic Acid Conformation; D013936:Thymidine / Q000031:analogs & derivatives*; D013941:Thymine / Q000737:chemistry
chemical_list: D000998:Antiviral Agents; D001643:Bridged Bicyclo Compounds; D054329:Carbasugars; D013941:Thymine; D013936:Thymidine