A greener enantioselective synthesis of the antiviral agent North-methanocarbathymidine (N-MCT) from 2-deoxy-d-ribose.

Tetrahedron
Olaf R Ludek, Victor E Marquez

Abstract

An enantioselective synthesis of suitably protected (1R,2S,4S,5S)-4-amino-1-(hydroxymethyl)bicyclo[3.1.0]hexan-2-ol, a key starting material for the synthesis of conformationally locked carbocyclic nucleosides, including the antiviral active North-methanocarba thymidine, is reported. Starting from 2-deoxyribose the target Boc-protected amine was prepared in 33% overall yield under condition that are ecologically friendlier than previous methods.

References

Mar 30, 2006·Antimicrobial Agents and Chemotherapy·Mark N PrichardEarl R Kern

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Citations

Jul 24, 2014·Organic Letters·Elena Yu SchmidtYurii V Gatilov
Jun 1, 2012·Organic & Biomolecular Chemistry·Adrian OrtizDavid A Conlon
Mar 9, 2013·Chemical Society Reviews·Omar BoutureiraSergio Castillón
May 4, 2012·Medicinal Research Reviews·Erik De Clercq
Dec 21, 2012·Chemistry : a European Journal·Gaëlle MalikDavid Crich
Oct 29, 2015·The Journal of Antibiotics·Magdalena SoluchBartłomiej Furman
May 26, 2021·The Journal of Organic Chemistry·Emanuele CasaliGiuseppe Zanoni

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