Thiosugars, 17. Preparation and structure of a novel deoxythionucleoside

Author:

Voss Jürgen1,Otzen Dirk2,Adiwidjaja Gunadi2

Affiliation:

1. Department of Chemistry, Organic Chemistry , University of Hamburg, Martin-Luther-King-Platz 6 , D-20146 Hamburg , Germany

2. Department of Chemistry, Organic Chemistry , University of Hamburg , D-20146 Hamburg , Germany

Abstract

Abstract 1-(3′,5′-Anhydro-2′-deoxy-3′-thio-D-lyxo-furanosyl)thymine is prepared from the corresponding methyl pentofuranoside by using the silyl Hilbert–Johnson reaction. The α- and β-anomers are separated by column chromatography and their configuration is elucidated by NMR spectroscopy and, in case of the α-anomer, by an X-ray structure determination.

Publisher

Walter de Gruyter GmbH

Subject

General Chemistry

Reference20 articles.

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2. R. T. Walker in 4′-Thio-2′-Deoxyribonucleosides, Their Chemistry and Biological Properties – A Review in Anti-infectives: Recent Advances in Chemistry and Structure-Activity Relationships, Vol. 198 (Eds.: P. H. Bentley, P. J. O’Hanlon), Special Publication, The Royal Society of Chemistry, Cambridge, 1997, p. 203.

3. H. Vorbrüggen, C. Ruh-Pohlenz, Handbook of Nucleoside Synthesis, John Wiley & Sons, Chichester, 2001.

4. M. Yokoyama in The Properties of 4′-Thionucleosides in Modified Nucleosides; Biochemistry, Biotechnology and Medicine (Ed.: P. Herdewijn), Wiley-VCH, Weinheim, 2008, p. 173.

5. V. A. Mulamoottil, M. S. Majik, G. Chandra, L. S. Jeong in Recent Advances in Synthesis and Biological Activity of 4′-Thionucleosides, in Chemical Synthesis of Nucleoside Analogues (Ed.: P. Mercino), John Wiley & Sons, Hoboken, 2013, p. 655.

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