1,6-Anhydro-1-thio-β-D-glucopyranose (Thiolevoglucosan) and the Corresponding Sulfoxides and Sulfone

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Title:1,6-Anhydro-1-thio-β-D-glucopyranose (Thiolevoglucosan) and the Corresponding Sulfoxides and Sulfone
Creators:
Buděšínský, Miloš
Poláková, Jana
Hamerníková, Michaela
Císařová, Ivana
Trnka, Tomáš
Černý, Miloslav
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 71, 3, pp. 311-336
Uncontrolled Keywords:Conformation analysis, X-Ray diffraction, Pummerer rearrangement, Magnetic anisotropy of sulfinyl group, Anhydro sugars, Sulfones, NMR spectroscopy, Sulfoxides, Carbohydrates, Thio sugars

Abstract

Starting 1,2,3,4-tetra-<i>O</i>-acetyl-6-<i>O</i>-tosyl-β-D-glucopyranose (<strong>3</strong>) was converted into 2,3,4-tri-<i>O</i>-acetyl-1-thio-6-<i>O</i>-tosyl-β-D-glucopyranose (<strong>6</strong>) via intermediate glycosyl bromide <strong>4</strong> and <i>S</i>-thiouronium salt <strong>5</strong>. Treatment of compound <strong>6</strong> with sodium methoxide gave 1,6-anhydro-1-thio-β-D-glucopyranose (thiolevoglucosan <strong>2a</strong>). The isomeric sulfoxides <strong>7</strong> and <strong>8</strong> were prepared by selective oxidation of thiolevoglucosan <strong>2a</strong> with hydrogen peroxide or 3-chloroperoxybenzoic acid. The structure of new compounds was confirmed by <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy or by X-ray analysis; magnetic anisotropy of the sulfinyl and sulfonyl group has been discussed. <p>

Title:1,6-Anhydro-1-thio-β-D-glucopyranose (Thiolevoglucosan) and the Corresponding Sulfoxides and Sulfone
Creators:
Buděšínský, Miloš
Poláková, Jana
Hamerníková, Michaela
Císařová, Ivana
Trnka, Tomáš
Černý, Miloslav
Uncontrolled Keywords:Conformation analysis, X-Ray diffraction, Pummerer rearrangement, Magnetic anisotropy of sulfinyl group, Anhydro sugars, Sulfones, NMR spectroscopy, Sulfoxides, Carbohydrates, Thio sugars
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:3
Page Range:pp. 311-336
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20060311UNSPECIFIED
ID Code:2482
Item Type:Article
Deposited On:06 Feb 2009 17:19
Last Modified:06 Feb 2009 16:19

Citation

Buděšínský, Miloš; Poláková, Jana; Hamerníková, Michaela; Císařová, Ivana; Trnka, Tomáš; Černý, Miloslav (2006) 1,6-Anhydro-1-thio-β-D-glucopyranose (Thiolevoglucosan) and the Corresponding Sulfoxides and Sulfone. Collection of Czechoslovak Chemical Communications, 71 (3). pp. 311-336. ISSN 0010-0765

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