Unit

UNIT 1.29 Synthesis of a North-Methanocarba-Thymidine (N-MCT) Analog

  1. Andrew Thompson1,
  2. Victor E. Marquez2

Published Online: 1 DEC 2012

DOI: 10.1002/0471142700.nc0129s51

Current Protocols in Nucleic Acid Chemistry

Current Protocols in Nucleic Acid Chemistry

How to Cite

Thompson, A. and Marquez, V. E. 2012. Synthesis of a North-Methanocarba-Thymidine (N-MCT) Analog. Current Protocols in Nucleic Acid Chemistry. 51:1.29:1.29.1–1.29.14.

Author Information

  1. 1

    J-Star Research, Inc., South Plainfield, New Jersey

  2. 2

    Chemical Biology Laboratory, Frederick National Laboratory for Cancer Research, NIH, Frederick, Maryland

Publication History

  1. Published Online: 1 DEC 2012

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. Curr. Protoc. Nucleic Acid Chem. 51:1.29.1-1.29.14. © 2012 by John Wiley & Sons, Inc.

Keywords:

  • carbocyclic nucleosides;
  • bicyclo[3.1.0]hexane nucleosides;
  • conformationally locked;
  • antiviral