Synthesis of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino- and 1,6-Anhydro-2,3,4-trideoxy-3,4-epimino-β-D-hexopyranoses and Their NMR and Infrared Spectra

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Title:Synthesis of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino- and 1,6-Anhydro-2,3,4-trideoxy-3,4-epimino-β-D-hexopyranoses and Their NMR and Infrared Spectra
Creators:
Karban, Jindřich
Buděšínský, Miloš
Kroutil, Jiří
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 69, 10, pp. 1939-1954
Uncontrolled Keywords:Pyramidal inversion, Infrared spectroscopy, Aziridines, 1,6-Anhydro-β-D-hexopyranoses, Anhydrosugars, Aminosugars, Azides, Carbohydrates, NMR spectroscopy

Abstract

A complete series of 2,3,4-trideoxy-2,3-epimino and 2,3,4-trideoxy-3,4-epimino derivatives of 1,6-anhydro-β-D-hexopyranoses were prepared by lithium aluminium hydride reduction of vicinal <i>trans</i> azido tosylates. Unusual formation of the aziridine ring from precursors with the <i>trans</i>-diequatorial arrangement of the reacting groups was observed. NMR and infrared spectra of the aziridines are discussed. <p>

Title:Synthesis of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino- and 1,6-Anhydro-2,3,4-trideoxy-3,4-epimino-β-D-hexopyranoses and Their NMR and Infrared Spectra
Creators:
Karban, Jindřich
Buděšínský, Miloš
Kroutil, Jiří
Uncontrolled Keywords:Pyramidal inversion, Infrared spectroscopy, Aziridines, 1,6-Anhydro-β-D-hexopyranoses, Anhydrosugars, Aminosugars, Azides, Carbohydrates, NMR spectroscopy
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:69
Number:10
Page Range:pp. 1939-1954
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20041939UNSPECIFIED
ID Code:2313
Item Type:Article
Deposited On:06 Feb 2009 17:17
Last Modified:06 Feb 2009 16:17

Citation

Karban, Jindřich; Buděšínský, Miloš; Kroutil, Jiří (2004) Synthesis of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino- and 1,6-Anhydro-2,3,4-trideoxy-3,4-epimino-β-D-hexopyranoses and Their NMR and Infrared Spectra. Collection of Czechoslovak Chemical Communications, 69 (10). pp. 1939-1954. ISSN 0010-0765

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