Per-O-t-Butyldimethylsilyl-beta-D-Galactofuranose: A Versatile Glycosylating Agent for Galactofuranosylation

GONZÁLEZ SALAS, D.; GUBERMAN, M.; MARINO, C.

Carbohydrate Chemistry: Proven Methods 4

CRC Press

Año: 2017; p. 133 - 140

Due to the presence of D-galactofuranose (D-Galf) in glycoconjugates of microorganisms, many of them pathogenic, the synthesis of galactofuranosyl containing molecules is of great interest.1 Glycoconjugates, glycomimetics and synthetic oligosaccharides containing D-Galf units are valuable tools for elucidating the mechanisms of action of the enzymes related to this sugar and for the identification and design of new therapeutic agents.The chemical synthesis of such compounds requires efficient preparation of glycosyl donors for introduction of the D-Galf moiety into the target molecules (galactofuranosylation). In order to obtain such materials free from the pyranosic forms, many of the synthesis described involve more than one step or chromatographic procedures.2In this chapter we describe the synthesis of 1,2,3,5,6-penta-O-tert-butyl(dimethyl)silyl-β-D-galactofuranose (1), obtained as a crystalline product in just one high yielding step from D-galactose (Scheme 1).3