engleski

Synthesis of 5-hydroxymethylbenzopsoralen glucoside

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-?-D-glucopyranosyloxymethyl)-2H-benzofuro?3,2-g?-1-benzopyran-2-one (benzopsoralen acetylated glucoside, BP-OAG, 7), which after deacetylation yielded the free glucoside 8. Different synthetic approaches were tried to accomplish glycosidation, including Ag2CO3, 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.

benzopsoralen glucoside; 5-(?-D-glucopyranosyloxymethyl)-2H-benzofuro?3;2-g?-1-benzopyran-2-one; glucosidation; Koenigs-Knorr reaction

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