Synthesis of Galloylglucose Analogues

• Main Author: 顏志政
• Other Authors: 陳繼明
• Format: Others
• Language: zh-TW
• Published: 1995
• Online Access: http://ndltd.ncl.edu.tw/handle/11917229978355402848

碩士 === 台北醫學大學 === 藥學研究所 === 83 === 　　Galloyglucoses are a group of phenolic compounds widely distributed in the plant kingdom. Structurally, they are characterized by several molecules of gallic acid attached to a β-D-glucopyranose through ester linkage. Recent reports indicated galloylglucoses displaying antibacterial activity, lowering the level of blood urea nitrogen, inhibiting of lipid peroxidation and inhibition the activity of angiotensin converting enzyme.We wish to report the synthesis of galloylglucose analoges by incorporation of phenlic benzoyl and cinnamoyl moeity into D-glucoses molecule and these phenolic compounds will be evaluated their activity on cardiovascular system. 　　Coupling of methyl α-D-glucopyranoside with tetrahydropytanyl or benzyl protected hydroxy group in substituted cinnamic acids and benzlic using the Keck modification of the Steglich esterfication oumaroyl the glucose esters in isolated yield of 50%-90%. Following cleavage of tetrahydropyranyl and benzyl proteitiog groups by strong acidic resin and hydrogenation, respectively, afforded the final products. They are methyl 2,3,4,6-tetra(hydroxybenzoyl)-α-D-glucopyranoside(la), methyl 2,3,4,6-tetraprotocatechuoyl-α-D-glucopyranoside(lb), methyl 2,3,4,6-tetragalloyl-α-D-glucopyranoside (lc), methyl 2,3,4,6-tetracaffeoyl-α-D-glucopyranoside(ld), methyl 2,3,4,6-tetracaffelyl-α-D-glucopyranoside (le), and methyl 2,3,4,6-tetraferuloyl-α-D-glucopyranoside(lf). 　　The structures of these compounds are consistent with their spectral data of the IR,1H-NMR,BC-NNR and Mass spectra.