Synthesis of a New Type of d-Mannosamine Glycosyl Donor and Acceptor and
their Use for the Preparation of Oligosaccharides Consisting of d-Mannosamine Units Linked by α(1→4)-Glycosidic
Bonds

Matyáš Turský; Jan Veselý; Iva Tišlerová; Tomáš Trnka; Miroslav Ledvina

doi:10.1055/s-2008-1067197

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Synthesis 2008(16): 2610-2616
DOI: 10.1055/s-2008-1067197

PAPER

Synthesis of a New Type of d-Mannosamine Glycosyl Donor and Acceptor and their Use for the Preparation of Oligosaccharides Consisting of d-Mannosamine Units Linked by α(1→4)-Glycosidic Bonds

Matyáš Turský^a,b,1, Jan Veselý^a, Iva Tišlerová^a, Tomáš Trnka^a, Miroslav Ledvina*^b
^a Department of Organic and Nuclear Chemistry, Faculty of Science, Charles University, Albertov 2030, 128 43 Prague 2, Czech Republic
^b Laboratory of Glycoconjugates, Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic
Fax: +420(2)20183560; e-Mail: ledvina@uochb.cas.cz;

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Publication History

Received 1 February 2008
Publication Date:
25 July 2008 (online)

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Abstract

Herein, we present the synthesis of three new 2-azido-2-deoxy-d-mannopyranose building blocks that are useful in the preparation of oligosaccharides consisting of α(1→4)-linked 2-azido-2-deoxy-d-mannopyranose units. The successful utilization of these intermediates in the stepwise synthesis of the corresponding trisaccharide is also described in detail.

Key words

carbohydrates - glycosylation - oligosaccharides - d-mannosamine