Naslov
Synthesis of 5-hydroxymethylbenzopsoralen glucoside

Autori
Zorc, Branka ; Jadrijević-Mladar Takač, Milena ; Rodighiero, Paolo

Izvornik
Acta pharmaceutica (1330-0075) 49 (1999), 1; 11-19

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Benzopsoralen glucoside; 5-(beta-D-glucopyranosyloxymethyl)-2H-benzofuro[3; 2-g]-1-benzopyran-2-one; Glucosidation; Koenigs-Knorr reaction

Sažetak
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 (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.

Izvorni jezik
Engleski

Znanstvena područja
Farmacija

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