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.
A detailed protocol for the synthesis of North-methanocarba-thymidine (n class="Chemical">N-MCT), a potent antiviral nucleoside with a restricted bicyclo[3.1.0]hexanepseudosugar conformation, is presented. The process is described in two parts. The first basic protocol deals with the synthesis of the carbobicyclicpseudosugar 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: Zhengrong Wu; Melissa Maderia; Joseph J Barchi; Victor E Marquez; Ad Bax Journal: Proc Natl Acad Sci U S A Date: 2004-12-23 Impact factor: 11.205
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