Acta Pharm. 49 (1999) 11-19
Benzopsoralen derivative, 5-hydroxymethyl-2H-benzofuro[3,2-g]-1- benzopyran-2-one (BP-OH, 1) and its 5-bromomethyl analogue (BP-Br, 3) were transformed to the corresponding glucoside, 5-(2,3,4,6-tetra-O-beta-D- glucopyranosyloxymethyl)-2H-benzofuro[3,2-g]-1-benzopyran-2-one (benzopsoralenacetylated glucoside, BP-OAG, 7), which after deacetylation yielded the free glucoside 8. Different synthetic approaches were tried to accomplish glycosidation, including Ag2 CO3, HgO/HgCl2, Hg(CN)2 or BF3×Et2O as aglycone and carbohydrate moiety condensation promotors. Hg(CN)2 was found to give significantly better yield (70%) on the product 7 than other mercury and silver salts or BF3×Et2O.
Keywords: benzopsoralen glucoside, 5-(beta-D-glucopyranosyloxymethyl) -2H-benzofuro[3,2-g]-1-benzopyran-2-one, glucosidation, Koenigs-Knorr reaction