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Synthesis and X-ray studies of novel 3-C-nitromethyl-hexofuranoses.

Authors
  • Turks, Māris1
  • Vēze, Krista2
  • Kiseļovs, Gļebs3
  • Mackeviča, Jevgeņija2
  • Lugiņina, Jevgeņija2
  • Mishnev, Anatoly3
  • Marković, Dean4
  • 1 Faculty of Material Science and Applied Chemistry, Riga Technical University, 3 P. Valdena Str., Riga LV-1007, Latvia. Electronic address: [email protected] , (Latvia)
  • 2 Faculty of Material Science and Applied Chemistry, Riga Technical University, 3 P. Valdena Str., Riga LV-1007, Latvia. , (Latvia)
  • 3 Latvian Institute of Organic Synthesis, 21 Aizkraukles Str., Riga LV-1006, Latvia. , (Latvia)
  • 4 Department of Biotechnology, University of Rijeka, Trg braće Mažuranića 10, 51000 Rijeka, Croatia. , (Croatia)
Type
Published Article
Journal
Carbohydrate research
Publication Date
Jun 04, 2014
Volume
391
Pages
82–88
Identifiers
DOI: 10.1016/j.carres.2014.03.003
PMID: 24785391
Source
Medline
Keywords
License
Unknown

Abstract

A practical method for the synthesis of three novel 3-C-nitromethyl-hexofuranoses is reported. The Henry reaction on a 1,2:5,6-di-O-isopropylidene-α-d-gulofuranose-derived ketone provided a 3-C-branched gulo-isomer as the sole reaction product. The dehydration-rehydration of the latter yielded an isopropylidene-protected 3-C-nitromethyl-galactofuranose. The reaction sequence can be also used for the synthesis of a 3-deoxy-3-C-nitromethyl-hexofuranose derivative with a gulo-configuration. Two of the newly obtained carbohydrate derivatives were characterized by X-ray crystallography.

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