Preparation and Reactions of 2-Chloroethyl 1-Thio-β-D-glycopyranosides Derived from D-Galactose, D-Glucose, and 2-Acetamido-2-deoxy-D-glucose

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Title:Preparation and Reactions of 2-Chloroethyl 1-Thio-β-D-glycopyranosides Derived from D-Galactose, D-Glucose, and 2-Acetamido-2-deoxy-D-glucose
Creators:
Černý, Miloslav
Trnka, Tomáš
Buděšínský, Miloš
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 61, 10, pp. 1489-1500
Uncontrolled Keywords:<sup>1</sup>H and <sup>13</sup>C NMR, 2-Halogenoethyl thioglycosides, Synthesis, Mechanism of hydrolysis, Nucleophilic substitution

Abstract

Chloroethyl 1-thio-β-D-glycopyranosides of the D-<i>galacto </i>and D-<i>gluco </i>configurations <strong>5a-5c</strong> were prepared by alkylation of the corresponding 1-thio-β-D-hexopyranoses <strong>3a-3c</strong> with 1-bromo-2-chloroethane followed by deacetylation. The starting 1-thio-β-D-hexopyranoses were obtained from the acetylated glycopyranosyl halides <i>via</i> isothiouronium salts. It was demonstrated that the chloroethyl thioglycosides <strong>5a-5c</strong> undergo hydrolysis in aqueous solutions to give the 2-hydroxyethyl thioglycosides <strong>6a-6c</strong> and reducing hexoses and that this hydrolysis proceeds via episulfonium salts. The hydrolysis was monitored by <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy. In 1% aqueous solutions of sodium carbonate containing phenol or aniline, the thioglycosides <strong>5a-5c</strong> provide, in addition to the above hydrolysis products, also the phenoxyethyl and phenylaminoethyl thioglycosides <strong>9a</strong>, <strong>10a</strong> and <strong>9b</strong>, <strong>10b</strong>, respectively.

Title:Preparation and Reactions of 2-Chloroethyl 1-Thio-β-D-glycopyranosides Derived from D-Galactose, D-Glucose, and 2-Acetamido-2-deoxy-D-glucose
Creators:
Černý, Miloslav
Trnka, Tomáš
Buděšínský, Miloš
Uncontrolled Keywords:<sup>1</sup>H and <sup>13</sup>C NMR, 2-Halogenoethyl thioglycosides, Synthesis, Mechanism of hydrolysis, Nucleophilic substitution
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:61
Number:10
Page Range:pp. 1489-1500
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19961489UNSPECIFIED
ID Code:1052
Item Type:Article
Deposited On:06 Feb 2009 17:06
Last Modified:06 Feb 2009 16:06

Citation

Černý, Miloslav; Trnka, Tomáš; Buděšínský, Miloš (1996) Preparation and Reactions of 2-Chloroethyl 1-Thio-β-D-glycopyranosides Derived from D-Galactose, D-Glucose, and 2-Acetamido-2-deoxy-D-glucose. Collection of Czechoslovak Chemical Communications, 61 (10). pp. 1489-1500. ISSN 0010-0765

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