Preparation of Ethyl 2-Azido-2-deoxy-1-thio-β-d-mannopyranosides, and their Rearrangement to 2-S-Ethyl-2-thio-β-d-mannopyranosylamines

Jan Veselý; Anna Rohlenová; Martina Džoganová; Tomáš Trnka; Iva Tišlerová; David Šaman; Miroslav Ledvina

doi:10.1055/s-2006-926297

PAPER

Preparation of Ethyl 2-Azido-2-deoxy-1-thio-β-d-mannopyranosides, and their Rearrangement to 2-S-Ethyl-2-thio-β-d-mannopyranosylamines

Jan Veselý^a, Anna Rohlenová^b, Martina Džoganová^a, Tomáš Trnka^a, Iva Tišlerová^a, David Šaman^b, Miroslav Ledvina*^b
^a Department of Organic Chemistry, Charles University, Albertov 2030, 128 40 Prague 2, Czech Republic
^b Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic
Fax: +420 220183560; e-Mail: ledvina@uochb.cas.cz;

Abstract

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Abstract

The synthesis of ethyl 2-azido-2-deoxy-1-thio-β-d-mannopyranosides 7-11, starting from appropriate synthons with gluco configuration, via S_N2 substitution at C(2), and their rearrangement to 2-S-ethyl-2-thio-β-d-mannopyranosylamines 12-14 are presented.

Key words

carbohydrates - d-mannosamine - thioglycosides - stereoselective synthesis - intramolecular rearrangements

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