124662-85-7Relevant academic research and scientific papers
SYNTHESIS OF GALACTOFURANOSE DISACCHARIDES OF BIOLOGICAL SIGNIFICANCE
Marino, Carla,Varela, Oscar,Lederkremer, Rosa M. De
, p. 65 - 76 (1989)
Methyl β-D-galactofuranoside (3) was readily obtained by tin(IV) chloride-catalyzed glycosylation of penta-O-benzoyl-α,β-D-galactofuranose (1), followed by debenzoylation with sodium methoxide.Glycosylation of 1 with 2,3,5-tri-O-benzoyl-D-galactono-1,4-la
Convenient syntheses of 5-O- and 3,5-di-O-(β-D-galactofuranosyl)-D-galactofuranose
Lederkremer, Rosa M. de,Marino, Carla,Varela, Oscar
, p. 227 - 235 (2007/10/02)
Benzoylation of D-galactono-1,4-lactone with 2.2 mol of benzoyl chloride, at -23 deg C, gave the 2,6-dibenzoate (2, 62percent).Tin(IV) chloride-catalyzed glycosylation of 2 with 1,2,3,5,6-penta-O-benzoyl-α,β-D-galactofuranose (1) afforded 2,6-di-O-benzoyl-5-O-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-D-galactono-1,4-lactone (4, 70percent), HO-3 of which was benzoylated to give 5.The structure of 4 was confirmed by its conversion into crystalline β-D-Gal f-(1->5)-D-Gal-ol (8).Reduction of the lactone function of 5 with di-isoamylborane followed by debenzoylation gave β-D-Gal f-(1->5)-D-Gal f (7).A by-product of the condensation of 1 with 2 was characterized as 2,6-di-O-benzoyl-3,5-di-O-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-D-galactono-1,4-lactone (9), which was converted, as for 5, into β-D-Gal f-(1->3)-D-Gal f (13).
