One-Step Syntheses of 1,2,3,5,6-Penta-O-Benzoyl-alpha, beta-D-Galactofuranose and 1,2,3,5-Tetra-O-Benzoyl-alpha, beta-D-Arabinofuranose.

CARLA, MARINO; LUCÍA, GANDOLFI DONADÍO; CAROLA, GALLO-RODRÍGUEZ; BAI, YU; ROSA, M. DE LEDERKREMER

Carbohydrate Chemistry, Proven Synthetic Methods Volume 1

Taylor and francis group, LLC

Lugar: Boca Raton; Año: 2010; p. 231 - 238

D-Arabinofuranose (Araf) and D-galactofuranose (Galf) are found in the arabinogalactan of the cell wall of mycobacteria.1,2 D-Galf is also present in glycoconjugates of infectious protozoa like Trypanosoma cruzi and Leishmania,3,4 and of fungi.5,6 The chemistry and biology of arabinofuranosyl and galactofuranosyl containing polysaccharides has been reviewed.7 The furanose form of arabinose and galactose is absent in mammals, hence the interest of several groups in the synthesis of the oligosaccharides containing these sugars for metabolic and immunological studies. Per-O-acylated monosaccharides are important synthons for the synthesis of glycosides, in particular oligosaccharides.8 We have used galactofuranose per-O-benzoate for the first synthesis of a-D-Galf phosphate9 and 1-thio-b-D-galactofuranosides.10 Also, Araf and Galf were introduced as the terminal quasi non-reducing (upstream) unit in oligosaccharides using the tin(IV) chloride promoted condensation.11,12