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Pregled bibliografske jedinice broj: 983

Synthesis of 5-hydroxymethylbenzopsoralen glucoside


Zorc, Branka; Jadrijević-Mladar Takač, Milena; Rodighiero, Paolo
Synthesis of 5-hydroxymethylbenzopsoralen glucoside // Acta pharmaceutica, 49 (1999), 1; 11-19 (međunarodna recenzija, članak, znanstveni)


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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-(?-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-?-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
Kemija



POVEZANOST RADA


Projekti:
006243

Ustanove:
Farmaceutsko-biokemijski fakultet, Zagreb


Citiraj ovu publikaciju:

Zorc, Branka; Jadrijević-Mladar Takač, Milena; Rodighiero, Paolo
Synthesis of 5-hydroxymethylbenzopsoralen glucoside // Acta pharmaceutica, 49 (1999), 1; 11-19 (međunarodna recenzija, članak, znanstveni)
Zorc, B., Jadrijević-Mladar Takač, M. & Rodighiero, P. (1999) Synthesis of 5-hydroxymethylbenzopsoralen glucoside. Acta pharmaceutica, 49 (1), 11-19.
@article{article, author = {Zorc, Branka and Jadrijevi\'{c}-Mladar Taka\v{c}, Milena and Rodighiero, Paolo}, year = {1999}, pages = {11-19}, keywords = {benzopsoralen glucoside, 5-(?-D-glucopyranosyloxymethyl)-2H-benzofuro?3, 2-g?-1-benzopyran-2-one, glucosidation, Koenigs-Knorr reaction}, journal = {Acta pharmaceutica}, volume = {49}, number = {1}, issn = {1330-0075}, title = {Synthesis of 5-hydroxymethylbenzopsoralen glucoside}, keyword = {benzopsoralen glucoside, 5-(?-D-glucopyranosyloxymethyl)-2H-benzofuro?3, 2-g?-1-benzopyran-2-one, glucosidation, Koenigs-Knorr reaction} }
@article{article, author = {Zorc, Branka and Jadrijevi\'{c}-Mladar Taka\v{c}, Milena and Rodighiero, Paolo}, year = {1999}, pages = {11-19}, keywords = {benzopsoralen glucoside, 5-(?-D-glucopyranosyloxymethyl)-2H-benzofuro?3, 2-g?-1-benzopyran-2-one, glucosidation, Koenigs-Knorr reaction}, journal = {Acta pharmaceutica}, volume = {49}, number = {1}, issn = {1330-0075}, title = {Synthesis of 5-hydroxymethylbenzopsoralen glucoside}, keyword = {benzopsoralen glucoside, 5-(?-D-glucopyranosyloxymethyl)-2H-benzofuro?3, 2-g?-1-benzopyran-2-one, glucosidation, Koenigs-Knorr reaction} }

Časopis indeksira:


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