Formylation of carbohydrates and the evolution of synthetic routes
to
artificial oligosaccharides and glycoconjugates*
Alessandro Dondoni
Laboratorio di Chimica Organica, Dipartimento di Chimica,
Università di Ferrara, Via Borsari 46, 44100 Ferrara, Italy
Abstract: 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 b-D-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.
*Lecture presented at the 13th International
Conference on Organic Synthesis (ICOS-13), Warsaw, Poland, 1-5 July
2000.
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