Formylation of carbohydrates and the evolution of synthetic routes to artificial oligosaccharides and glycoconjugates

A highly effective method for the synthesis of formyl C-glycosides is described via addition of 2-lithiothiazole or 2-lithiobenzothiazole to sugar lactones, deoxygenation of the resulting ketols, and releasing of the formyl group from the heterocyclic ring. The synthetic utility of these sugar aldeh...

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Bibliographic Details
Published inPure and applied chemistry Vol. 72; no. 9; pp. 1577 - 1588
Main Author Dondoni, Alessandro
Format Journal Article
LanguageEnglish
Published Berlin De Gruyter 01.01.2000
Walter de Gruyter GmbH
Subjects
Aldehydes
Carbohydrates
Deoxygenation
Disaccharides
Lactones
Oligomers
Oligosaccharides
Synthesis
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Summary:A highly effective method for the synthesis of formyl C-glycosides is described via addition of 2-lithiothiazole or 2-lithiobenzothiazole to sugar lactones, deoxygenation of the resulting ketols, and releasing of the formyl group from the heterocyclic ring. The synthetic utility of these sugar aldehydes is demonstrated by the development of synthetic methods to more elaborate C-glycosides. These include various (1-6)-C-disaccharides and some higher oligomers up to a C,C,C,C-pentasaccharide; C-glycosyl amino acid isosteres of N-glycosyl asparagines; the methylene isostere of β-Δ-galactosyl ceramide; linear and cylic (2-1)-ketoside oligomers. An alternative synthesis of ethylene-bridged glycosyl asparagine isosteres is illustrated by the use of ethynyl C-glycosides as starting materials.
ISSN:0033-4545
1365-3075
DOI:10.1351/pac200072091577