2-Haloethyl 1-Thioglycosides as New Tools in Glycoside Syntheses. Part 1: Preparation, Characteristics, General Reactions

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Title:2-Haloethyl 1-Thioglycosides as New Tools in Glycoside Syntheses. Part 1: Preparation, Characteristics, General Reactions
Creators:
Krüger, Andreas
Pyplo-Schnieders, Jutta
Redlich, Hartmut
Winkelmann, Pär
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 69, 10, pp. 1843-1876
Uncontrolled Keywords:Protecting groups, Glycosidation, Leaving groups, Disaccharides, Thioglycosides, Glycosides, Carbohydrates

Abstract

2-Haloethyl 1-thioglycosides are excellent leaving groups when the 2-haloethyl function is activated with silver salts or Lewis acids. These thioglycosides can be synthesized on the original Černý route or for better compatibility with the needs of a more complex glycoside synthesis, in stepwise procedures via 2-(2-tetrahydropyran-2-yloxy)ethyl glycosides or trityl 1-thioglycosides. The initial step in glycosidation reaction presumably proceeds via a thiiranium ion, which is responsible for their increased reactivity compared with normal thioethers as leaving groups in glycoside syntheses. Basic features of this new system with respect to reactivity and selectivity in disaccharide syntheses are described. <p>

Title:2-Haloethyl 1-Thioglycosides as New Tools in Glycoside Syntheses. Part 1: Preparation, Characteristics, General Reactions
Creators:
Krüger, Andreas
Pyplo-Schnieders, Jutta
Redlich, Hartmut
Winkelmann, Pär
Uncontrolled Keywords:Protecting groups, Glycosidation, Leaving groups, Disaccharides, Thioglycosides, Glycosides, 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:69
Number:10
Page Range:pp. 1843-1876
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20041843UNSPECIFIED
ID Code:2309
Item Type:Article
Deposited On:06 Feb 2009 17:17
Last Modified:06 Feb 2009 16:17

Citation

Krüger, Andreas; Pyplo-Schnieders, Jutta; Redlich, Hartmut; Winkelmann, Pär (2004) 2-Haloethyl 1-Thioglycosides as New Tools in Glycoside Syntheses. Part 1: Preparation, Characteristics, General Reactions. Collection of Czechoslovak Chemical Communications, 69 (10). pp. 1843-1876. ISSN 0010-0765

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