Preparation of O-, S- and N-Benzyl Derivatives of 1,6-Anhydro-β-D-hexopyranoses via Aziridine Ring Opening

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Title:Preparation of O-, S- and N-Benzyl Derivatives of 1,6-Anhydro-β-D-hexopyranoses via Aziridine Ring Opening
Creators:
Kroutil, Jiří
Karban, Jindřich
Trnka, Tomáš
Buděšínský, Miloš
Černý, Miloslav
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 67, 12, pp. 1805-1819
Uncontrolled Keywords:Nucleophilic additions, Stereospecific synthesis, Anhydro sugars, Ring opening reactions, Amino sugars, Aziridines, NMR spectroscopy, Carbohydrates

Abstract

The aziridine ring opening of <i>N</i>-tosylepimino carbohydrates <strong>1</strong>-<strong>6</strong> having D-<i>allo</i>, D-<i>manno</i>, D-<i>galacto</i> and D-<i>talo</i> configurations with benzyl alcohol, benzylamine and phenylmethanethiol afforded 2-, 3- and 4-<i>O</i>-benzyl-, benzylsulfanyl and benzylamino derivatives of 1,6-anhydro-β-D-hexopyranoses of D-<i>gluco</i>, D-<i>galacto</i> and D-<i>manno</i> configurations <strong>7</strong>-<strong>23</strong> in 44-99% yields. Hexenopyranoses <strong>24</strong>-<strong>26</strong> were prepared from tosylepimino carbohydrates <strong>1</strong>, <strong>4</strong> and <strong>5</strong> by intramolecular rearrangement of the aziridine ring. <p>

Title:Preparation of O-, S- and N-Benzyl Derivatives of 1,6-Anhydro-β-D-hexopyranoses via Aziridine Ring Opening
Creators:
Kroutil, Jiří
Karban, Jindřich
Trnka, Tomáš
Buděšínský, Miloš
Černý, Miloslav
Uncontrolled Keywords:Nucleophilic additions, Stereospecific synthesis, Anhydro sugars, Ring opening reactions, Amino sugars, Aziridines, 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:67
Number:12
Page Range:pp. 1805-1819
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20021805UNSPECIFIED
ID Code:2035
Item Type:Article
Deposited On:06 Feb 2009 17:15
Last Modified:06 Feb 2009 16:15

Citation

Kroutil, Jiří; Karban, Jindřich; Trnka, Tomáš; Buděšínský, Miloš; Černý, Miloslav (2002) Preparation of O-, S- and N-Benzyl Derivatives of 1,6-Anhydro-β-D-hexopyranoses via Aziridine Ring Opening. Collection of Czechoslovak Chemical Communications, 67 (12). pp. 1805-1819. ISSN 0010-0765

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