Facile synthesis of per-O-tort-butyldimethylsilyl-β-D-galactofuranose and efficient glyeosylation via the galactofuranosyl iodide

Article abstract of DOI:10.1021/jo8025274

The synthesis of crystalline per-0-TBS-β-D-galactofuranose (Aβ) 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 β-stereoselectivity. Under the mild conditions of this reaction labile protective groups, like acetals, and furanosyl linkages are preserved.