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Synthesis of isoacteoside, a dihydroxyphenylethyl glycoside
Authors:Toshinari Kawada  Ryuji Asano  Kozo Makino and Tomoyasu Sakuno
Institution:(1) Faculty of Agriculture, Tottori University, 4-101 Minami, Koyama, 680-0945 Tottori, Japan;(2) Present address: Human Technology Division, Eastern Hiroshima Prefecture Industrial Research Institute, Fukuyama, 721-0975 Hiroshima, Japan
Abstract:The total chemical synthesis of isoacteoside (1), 2-(3prime,4prime-dihydroxyphenyl)ethyl 6-O-caffeoyl-3-O-(agr-l-rhamnopyranosyl)-beta-d-glucopyranoside, is described. An acteoside acetate with benzyl groups at the catechols (3: 2-(3prime,4prime-dibenzyloxyphenyl)ethyl 2,6-di-O-acetyl-4-O-3prime,4prime-bis(O-benzyl)caffeoyl]-3-O-(agr-l-rhamnopyranosyl)-beta-d-glucopyranoside) was treated with a solution of methy-lamine in methanol (MeNH2 in MeOH) to perform both deacetylation and caffeoyl migration, affording an isoacteoside derivative with benzyl groups at the catechols4b: 2-(3prime,4prime-dibenzyloxyphenyl)ethyl 6-O-3prime,4prime-bis(O-benzyl) caffeoyl] -3-O-(agr-l-rhamnopyranosyl)-beta-d-glucopyranoside —in 34% yield. Debenzylation of4b was successfully accomplished by catalytic transfer hydrogenation using 1,4-cyclohexadiene to give the target compound isoacteoside (1) in 54% yield.1H and13C nuclear magnetic resonance spectral data of the synthesized isoacteoside (1) were identical with those of the natural isoacteoside isolated fromPaulownia tomentosa (Thumb.) Steud.Part of this research was presented at the 51st Annual Meeting of the Japan Wood Research Society, Tokyo, April 2001
Keywords:Wood extractives  Carbohydrates  Caffeic acid sugar ester  Dihydroxyphenylethyl glycoside  Phenylpropanoid glycoside
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