Synthesis of the (1-6)-linked thiodisaccharide of galactofuranose:

EVANGELINA REPETTO; CARLA MARINO; OSCAR VARELA

BIOORGANIC & MEDICINAL CHEMISTRY.

PERGAMON-ELSEVIER SCIENCE LTD

Lugar: Amsterdam; Año: 2013 p. 3327 - 3333

0968-0896

A new (1,6)-linked thiodisaccharide formed by two galactofuranosyl units has been synthesized. Methyl (methyl a,b-D-galactofuranosid)uronate was employed as the starting compound, which was per-O-silylated with TBSCl and reduced with LiAlH4 to afford methyl 2,3,5-tri-O-tert-butyldimethylsilyl-b-D-galactofuranoside (2b) as a key precursor for the preparation of methyl per-O-tert-butyldimethylsilyl-6-thio-b-D-galactofuranoside (12). The free thiol group of 12 was glycosylated and the product O-deprotected to afford the target b-D-Galf-S-(1,6)-b-D-Galf-OMe (14). The conformations of this thiodisaccharide were preliminarily studied using combined theoretical calculations and NMR data. Furthermore, the glycomimetic 14 showed to be a competitive inhibitor of the b-galactofuranosidase from Penicillum fellutanum (Ki = 3.62 mM).