7-羟基-4′-(β-D-吡喃葡萄糖苷基)葛根素的合成

Synthesis and Characterization of 7-Hydroxyl-4′-(β-D-glucopyranosyloxy)puerarin Derivatives

先将葡萄糖经酰化和溴化反应制备α-溴代四乙酰葡萄糖;再与葛根素在丙酮溶液中碳酸钾作用下醚化得到7-羟基-4-′(2,3,4,6-四乙酰基-β-D-吡喃葡萄糖苷基)葛根素,收率61.4%(以葛根素计);最后,将其进一步在甲醇溶液中与碳酸钠作用得到目标产物7-羟基-4-′(β-D-吡喃葡萄糖苷基)葛根素,收率90.5%。中间体和产物结构经1HNMR、MS确证。7-羟基-4-′(β-D-吡喃葡萄糖苷基)葛根素的水溶性与葛根素相比,提高了14.2倍。

Glucose via acylation and bromization pathway gives acetobromo-α-D-glucose.The etherification of puerarin to 7-hydroxyl-4′-（2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy） puerarin with acetobromo-α-D-glucose was carried out in acetone at the presence of potassium carbonate.The isolated yield was 61.4%（based on puerarin）.Finally,7-hydroxyl-4′-（β-D-glucopyranosyloxy）puerarin was obtained via deacetylation in anhydrous methanol at the presence of potassium carbonate with the isolated yield of 90.5%.The structures of intermediates and final product were characterized by 1HNMR spectra and MS.Compared with puerarin,the water-solubility of 7-hydroxyl-4′-（β-D-glucopyranosyloxy） puerarin was increased by 14.2 times.