Facile Synthesis of per-O-tertbutyldimethylsilyl-beta-D-Galactofuranose and Efficient Glycosylation via the Galactofuranosyl Iodide

BALDONI LUCIANA; MARINO, MARÍA CARLA

JOURNAL OF ORGANIC CHEMISTRY

Am. Chem. Soc.

Lugar: Washington DC; Año: 2009 vol. 74 p. 1994 - 2003

0022-3263

The synthesis of crystalline per-O-TBS-beta-D-galactofuranose as a new precursor of D-Galf units is described. Anomeric iodination by reaction with TMSI followed by in situ coupling with simple alcohols and a wide variety of glycosyl acceptors, in the absence of a promoter, was employed as a new efficient glycosylation method for the assembly of D-galactofuranosyl moieties with high beta-stereoselectivity. Under the mild conditions of this reaction labile protective groups, like acetals, and furanosyl linkages are preserved.