The synthesis of 4-O-oligoethylene glycol derivatives of 1,6-anhydro-β-D-glucopyranose and crown-ethers formed by their intramolecular cyclization

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Title:The synthesis of 4-O-oligoethylene glycol derivatives of 1,6-anhydro-β-D-glucopyranose and crown-ethers formed by their intramolecular cyclization
Creators:
Jindřich, Jindřich
Černý, Miloslav
Trnka, Tomáš
Buděšínský, Miloš
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 56, 12, pp. 2950-2963

Abstract

Using acid catalysed reaction of 1,6 : 3,4-dianhydro-2-O-<i>p</i>-toluenesulfonyl-β-D-galactopyranose (<i>I</i>) with mono-, di-, tri- and tetraethylene glycol, 4-O-oligoethylene glycol derivatives of 1,6-anhydro-2-O-<i>p</i>-toluenesulfonyl-β-D-glucopyranose <i>II - V</i> were obtained which were converted to 4-O-substituted 1,6 : 2,3-dianhydro-β-D-mannopyranones <i>VI - IX</i> under the effect of sodium hydroxide. Of them 4-O-(2-hydroxyethyl)- and 4-O-(11-hydroxy-3,6,9-trioxaundecyl) derivatives <i>VI</i> and <i>IX</i> were intramolecularly cyclized in basic medium under formation of 1,6-anhydro-3,4-O-ethlene-β-D-altropyranose (<i>X</i>) or 1,6-anhydro-2,4-O-(3,6,9-trioxaundecane-1,11-diyl)-β-D-glucopyranose (<i>XV</i>), respectively. Oxidation of the hydroxyl group in compound <i>XV</i> led to corresponding 3-ulose <i>XIX</i>, the reduction of which with sodium borohydride gave an isomer of compound <i>XV</i>, i.e. compound <i>XX</i> of D-<i>allo</i>-configuration. The structures of the compounds described in this paper were proved using <sup>1</sup>H and <sup>13</sup>C NMR spectra. Compounds <i>XV, XIX</i> and <i>XX</i> represent a new structural type of sugar crown-ethers.

Title:The synthesis of 4-O-oligoethylene glycol derivatives of 1,6-anhydro-β-D-glucopyranose and crown-ethers formed by their intramolecular cyclization
Creators:
Jindřich, Jindřich
Černý, Miloslav
Trnka, Tomáš
Buděšínský, Miloš
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:56
Number:12
Page Range:pp. 2950-2963
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19912950UNSPECIFIED
ID Code:5200
Item Type:Article
Deposited On:22 Feb 2010 11:32
Last Modified:22 Feb 2010 10:33

Citation

Jindřich, Jindřich; Černý, Miloslav; Trnka, Tomáš; Buděšínský, Miloš (1991) The synthesis of 4-O-oligoethylene glycol derivatives of 1,6-anhydro-β-D-glucopyranose and crown-ethers formed by their intramolecular cyclization. Collection of Czechoslovak Chemical Communications, 56 (12). pp. 2950-2963. ISSN 0010-0765

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