1-O-芳酰基-β-D-吡喃葡萄糖四乙酸酯和1-O-芳基-D-吡喃葡萄糖的立体选向合成

高等学校化学学报 ›› 1991, Vol. 12 ›› Issue (4): 482.

1-O-芳酰基-β-D-吡喃葡萄糖四乙酸酯和1-O-芳基-D-吡喃葡萄糖的立体选向合成

王世玉, 陈云东, 李翠娟, 金声

北京大学化学系, 100871

收稿日期:1989-03-06 出版日期:1991-04-24 发布日期:1991-04-24
通讯作者: 王世玉

Stereoselective Syntheses of　1-O-Aroyl-β-D-Glucopyranose Tetraacetates and 1-O-Aryl-D-Glucopyranose

Wang Shi-yu, Chen Yun-dong, Li Cui-juan, Jin Sheng

Department of Chemistry, Peking University, Beijing, 100871

Received:1989-03-06 Online:1991-04-24 Published:1991-04-24

摘要/Abstract

关键词: 1-O-芳酰基-&beta, -D吡喃葡萄糖四乙酸酯, 水杨酸甲酯-D-吡喃葡萄糖苷, 对-羟基苯甲酸甲酯-D-吡喃葡萄糖苷

Abstract: l-O-Aroyl-β-D-glucopyranose tetraacetates (Ⅰ-Ⅶ) were obtained by the condensation of tetra-O-acetyl-α-ZJ-glucopyranosyl bromide with aromatic acids in K₂CO₃-Me₂CO　at room temperature. Exclusive production of β-D-anomers was confirmed by measurement of their specific rotation and also by observing their 1R　and NMR　spectra. Reaction of α-acetobromoglucose with methyl o- or p-hydroxybenzoate in aq. KOH-Me₂CO　gives the corresponding β-D-glucopyranoside(Ⅶ-Ⅷ). Control of the stereochemistry in obtaining α-D-anomers (Ⅷ-Ⅸ) could also be satisfactorily achieved by employing penta-O-acetyl-D-glucopyranose and methyl o-or p-hydroxybenzoate in ZnG₂-AcOH-Ac₂O.

Key words: l-O-Aroyl-β-D-glucopyranose tetraacetate, Methyl salicylate-D-glucopyranoside, Methyl p-hydroxybenzoate-D-glucopyranoside

TrendMD:

王世玉, 陈云东, 李翠娟, 金声. 1-O-芳酰基-β-D-吡喃葡萄糖四乙酸酯和1-O-芳基-D-吡喃葡萄糖的立体选向合成. 高等学校化学学报, 1991, 12(4): 482.

Wang Shi-yu, Chen Yun-dong, Li Cui-juan, Jin Sheng . Stereoselective Syntheses of　1-O-Aroyl-β-D-Glucopyranose Tetraacetates and 1-O-Aryl-D-Glucopyranose. Chem. J. Chinese Universities, 1991, 12(4): 482.