Cleavage of the Epimines of 1,6-Anhydrohexoses with Fluoride Anion

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Title:Cleavage of the Epimines of 1,6-Anhydrohexoses with Fluoride Anion
Creators:
Kroutil, Jiří
Jeništová, Klára
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 70, 12, pp. 2075-2085
Uncontrolled Keywords:Fluorine, Aziridines, Cleavage reactions, Anhydrosugars, Fluorosugars, Aminosugars, Carbohydrates, NMR spectroscopy

Abstract

Aziridine ring cleavage reactions of five <i>N</i>-nosylepimines (<strong>2</strong>-<strong>6</strong>) having D-<i>talo</i>, D-<i>galacto</i>, D-<i>manno</i>, and D-<i>allo</i> configurations with potassium hydrogendifluoride under various reaction conditions have been performed. The cleavage regioselectively afforded diaxial isomers of vicinal amino-fluoro derivatives of 1,6-anhydro-β-D-gluco- and mannopyranose <strong>7</strong>-<strong>11</strong> in 51-94% yields. Removal of 2-nitrobenzenesulfonyl protecting group with benzenethiol has been attempted in the case of compound <strong>10</strong>. <p>

Title:Cleavage of the Epimines of 1,6-Anhydrohexoses with Fluoride Anion
Creators:
Kroutil, Jiří
Jeništová, Klára
Uncontrolled Keywords:Fluorine, Aziridines, Cleavage reactions, Anhydrosugars, Fluorosugars, Aminosugars, 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:70
Number:12
Page Range:pp. 2075-2085
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20052075UNSPECIFIED
ID Code:2457
Item Type:Article
Deposited On:06 Feb 2009 17:18
Last Modified:06 Feb 2009 16:18

Citation

Kroutil, Jiří; Jeništová, Klára (2005) Cleavage of the Epimines of 1,6-Anhydrohexoses with Fluoride Anion. Collection of Czechoslovak Chemical Communications, 70 (12). pp. 2075-2085. ISSN 0010-0765

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