Synthesis of Unsaturated Sulfur-Linked (1→4)-Disaccharides by Substitution of Tosyloxy Group in 1,6-Anhydro-3,4-dideoxy-2-O-tosyl-β-D-erythro-hex-3-enopyranose with 1-Thiohexopyranoses

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Title:Synthesis of Unsaturated Sulfur-Linked (1→4)-Disaccharides by Substitution of Tosyloxy Group in 1,6-Anhydro-3,4-dideoxy-2-O-tosyl-β-D-erythro-hex-3-enopyranose with 1-Thiohexopyranoses
Creators:
Bartoš, Petr
Černý, Miloslav
Tišlerová, Iva
Trnka, Tomáš
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 65, 11, pp. 1737-1744
Uncontrolled Keywords:<sup>1</sup>H NMR spectroscopy, Mass spectrometry, 1,6-Anhydrohexopyranoses, Allylic rearrangement, Unsaturated sulfur-linked dissaccharides, Thiosugars, Nucleophilic substitutions, Carbohydrates

Abstract

A novel method for the synthesis of unsaturated sulfur-linked (1→4)-disaccharides is described. The starting 1,6-anhydro-3,4-dideoxy-2-<i>O</i>-tosyl-β-D-<i>erythro</i>-hex-3-enopyranose (<strong>3</strong>) was reacted with potassium salt of acetylated 1-thiohexopyranoses of D-<i>gluco</i>-, D-<i>galacto</i>-, and L-<i>galacto</i>-configuration to give acetylated β-glycopyranosyl-(1→4)-1,6-anhydro-2,3-dideoxy-4-thio-β-D-<i>erythro</i>-hex-2-enopyranoses <strong>8</strong>-<strong>10</strong>. Their acid methanolysis under mild conditions afforded the corresponding methyl glycosides <strong>11</strong>-<strong>13</strong>. The structure of new compounds was confirmed by <sup>1</sup>H NMR and mass spectra data. <p>

Title:Synthesis of Unsaturated Sulfur-Linked (1→4)-Disaccharides by Substitution of Tosyloxy Group in 1,6-Anhydro-3,4-dideoxy-2-O-tosyl-β-D-erythro-hex-3-enopyranose with 1-Thiohexopyranoses
Creators:
Bartoš, Petr
Černý, Miloslav
Tišlerová, Iva
Trnka, Tomáš
Uncontrolled Keywords:<sup>1</sup>H NMR spectroscopy, Mass spectrometry, 1,6-Anhydrohexopyranoses, Allylic rearrangement, Unsaturated sulfur-linked dissaccharides, Thiosugars, Nucleophilic substitutions, 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:65
Number:11
Page Range:pp. 1737-1744
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20001737UNSPECIFIED
ID Code:1754
Item Type:Article
Deposited On:06 Feb 2009 17:12
Last Modified:06 Feb 2009 16:12

Citation

Bartoš, Petr; Černý, Miloslav; Tišlerová, Iva; Trnka, Tomáš (2000) Synthesis of Unsaturated Sulfur-Linked (1→4)-Disaccharides by Substitution of Tosyloxy Group in 1,6-Anhydro-3,4-dideoxy-2-O-tosyl-β-D-erythro-hex-3-enopyranose with 1-Thiohexopyranoses. Collection of Czechoslovak Chemical Communications, 65 (11). pp. 1737-1744. ISSN 0010-0765

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