Improved Synthesis of 1,2-trans-Acetates and 1,2-trans Ethyl 1-Thioglycosides Derived from 3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-D-hexopyranosides

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Title:Improved Synthesis of 1,2-trans-Acetates and 1,2-trans Ethyl 1-Thioglycosides Derived from 3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-D-hexopyranosides
Creators:
Veselý, Jan
Ledvina, Miroslav
Jindřich, Jindřich
Šaman, David
Trnka, Tomáš
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 68, 7, pp. 1264-1274
Uncontrolled Keywords:Glycoconjugates, Glycosyl donors, Aminosugars, Protecting groups, Thioglycosides, Glycosides, Phthalimide, Anomerisation, Carbohydrates

Abstract

Effective one-pot synthesis of 1,2-<i>trans</i>-acetates <strong>4b</strong>, <strong>5b</strong> and <strong>6a</strong> derived from <i>N</i>-phthaloyl-protected D-glucosamine, D-galactosamine and D-mannosamine, respectively, is presented. Anomerisation of the corresponding 1,2-<i>cis</i>-acetates <strong>4a</strong>, <strong>5a</strong> and <strong>6b</strong> and direct conversion of all of them to 1,2-<i>trans</i> ethyl 1-thioglycosides <strong>7</strong>, <strong>8</strong> and <strong>9</strong> are also described and discussed. <p>

Title:Improved Synthesis of 1,2-trans-Acetates and 1,2-trans Ethyl 1-Thioglycosides Derived from 3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-D-hexopyranosides
Creators:
Veselý, Jan
Ledvina, Miroslav
Jindřich, Jindřich
Šaman, David
Trnka, Tomáš
Uncontrolled Keywords:Glycoconjugates, Glycosyl donors, Aminosugars, Protecting groups, Thioglycosides, Glycosides, Phthalimide, Anomerisation, 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:68
Number:7
Page Range:pp. 1264-1274
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20031264UNSPECIFIED
ID Code:2118
Item Type:Article
Deposited On:06 Feb 2009 17:15
Last Modified:06 Feb 2009 16:15

Citation

Veselý, Jan; Ledvina, Miroslav; Jindřich, Jindřich; Šaman, David; Trnka, Tomáš (2003) Improved Synthesis of 1,2-trans-Acetates and 1,2-trans Ethyl 1-Thioglycosides Derived from 3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-D-hexopyranosides. Collection of Czechoslovak Chemical Communications, 68 (7). pp. 1264-1274. ISSN 0010-0765

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