Epoxide Migration and Pseudo-Epoxide Migration of 1,6:2,3- and 1,6:3,4-Dianhydro-β-D-hexopyranoses. Synthesis of Some Deoxy Halo Derivatives of 1,6-Anhydro-β-D-hexopyranoses

[img]PDF - Authorized users only
Language: English
169Kb
Title:Epoxide Migration and Pseudo-Epoxide Migration of 1,6:2,3- and 1,6:3,4-Dianhydro-β-D-hexopyranoses. Synthesis of Some Deoxy Halo Derivatives of 1,6-Anhydro-β-D-hexopyranoses
Creators:
Džoganová, Martina
Černý, Miloslav
Buděšínský, Miloš
Dračínský, Martin
Trnka, Tomáš
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 71, 10, pp. 1497-1515
Uncontrolled Keywords:Conformation analysis, Pseudo-epoxide migration, Epoxides, Anhydro sugars, Epoxide migration, DFT calculations, NMR spectroscopy, Carbohydrates

Abstract

Epoxide or pseudo-epoxide migration of 1,6:2,3-dianhydro- and 1,6:3,4-dianhydro-β-D-hexopyranoses was effected by treatment with aqueous sodium hydroxide or sodium iodide in acetone to give equilibrium mixtures. Various iodo derivatives of 1,6-anhydro-β-D-hexopyranoses were prepared as potential intermediates for pseudo-epoxide migration. NMR was used for following the reaction mechanism of epoxide and pseudo-epoxide migrations and analysis of reaction mixtures. Experimental data were compared with DFT calculations. Chair-boat equilibration of 1,6-anhydro-3-deoxy-3-halo-β-D-glucopyranoses was discussed. <p>

Title:Epoxide Migration and Pseudo-Epoxide Migration of 1,6:2,3- and 1,6:3,4-Dianhydro-β-D-hexopyranoses. Synthesis of Some Deoxy Halo Derivatives of 1,6-Anhydro-β-D-hexopyranoses
Creators:
Džoganová, Martina
Černý, Miloslav
Buděšínský, Miloš
Dračínský, Martin
Trnka, Tomáš
Uncontrolled Keywords:Conformation analysis, Pseudo-epoxide migration, Epoxides, Anhydro sugars, Epoxide migration, DFT calculations, NMR spectroscopy, Carbohydrates
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:71
Number:10
Page Range:pp. 1497-1515
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20061497UNSPECIFIED
ID Code:2557
Item Type:Article
Deposited On:06 Feb 2009 17:19
Last Modified:06 Feb 2009 16:19

Citation

Džoganová, Martina; Černý, Miloslav; Buděšínský, Miloš; Dračínský, Martin; Trnka, Tomáš (2006) Epoxide Migration and Pseudo-Epoxide Migration of 1,6:2,3- and 1,6:3,4-Dianhydro-β-D-hexopyranoses. Synthesis of Some Deoxy Halo Derivatives of 1,6-Anhydro-β-D-hexopyranoses. Collection of Czechoslovak Chemical Communications, 71 (10). pp. 1497-1515. ISSN 0010-0765

Repository Staff Only: item control page