Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2012 Dec:Chapter 1:Unit1.29.
doi: 10.1002/0471142700.nc0129s51.

Synthesis of a North-methanocarba-thymidine (N-MCT) analog

Andrew Thompson  1 , Victor E Marquez
Affiliations

Synthesis of a North-methanocarba-thymidine (N-MCT) analog

Andrew Thompson et al. Curr Protoc Nucleic Acid Chem. 2012 Dec.

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.

PubMed Disclaimer

Figures

Figure 1.29.1
Figure 1.29.1
Synthetic scheme of the carbobycyclic pseudosugar S.7.
Figure 1.29.2
Figure 1.29.2
Final, linear assembly of the thymine nucleobase to give N-MCT (S.12).
See this image and copyright information in PMC

References

    1. Biggadike K, Borthwick AD, Exall AM, Kirk BE, Roberts SM, Youds P, Slawin AMZ, and Williams DJ 1987. Synthesis of fluorinated carbocyclic nucleosides: Preparation of carbocyclic 1-(2’-deoxy-6’-fluororibofuranosyl)-5-iodouracils. J. Chem. Soc. Chem. Commun 255–256.
    1. Biggadike K, Borthwick AD, Evans D, Exall AM, Kirk BE, Roberts SM, Stephenson L, and Youds P. 1988. Use of diethylaminosulphur trifluoride (DAST) in the preparation of carobycyclic nucleosides. J. Chem. Soc. Perkin Trans. 1:549–554.
    1. Ezzitouni A, Russ P, and Marquez VE 1997. (1S,2R)-[(Benzyloxy) methyl] cyclopent-3-enol. A versatile synthon for the preparation of 4’,1’ a-methano- and 1’,1’a-methanocarbocyclic nucleosides. J. Org. Chem 62:4870–4873.
    1. Ludek OR and Marquez VE 2007. Convergent or linear? A challenging question in carbocyclic nucleoside chemistry. Synthesis 3451–3460.
    1. Madeira M, Shenoy S, Van QN, Marquez VE, and Barchi JJ Jr. 2007. Biophysical studies of DNA modified with conformationally constrained nucleotides: Comparison of 2-exo (north) and 3-exo (south) ‘locked’ templates. Nucleic Acids Res. 35:1978–1991. - PMC - PubMed

Publication types

MeSH terms

LinkOut - more resources