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溴代芳香碳糖苷的高效合成方法
  • 期刊名称:张云志,陈冠宇,陈国荣* 溴代芳香碳糖苷的高效合成方法 有机化学, 28(2)321-3249,20
  • 时间:0
  • 分类:O629.9[理学—有机化学;理学—化学]
  • 作者机构:[1]华东理工大学结构可控先进功能材料及其制备教育部重点实验室精细化工研究所,上海200237
  • 相关基金:国家自然科学基金(No.20576034)和上海市科学技术委员会(No.044307011)资助项目.
  • 相关项目:水、脂双溶性新颖碳糖复合物的嫁接合成
中文摘要:

天然黄酮碳糖苷化合物特有的稳定性和显著的生物活性,使其化学合成成为当今糖化学领域的研究热点之-.本工作立体专一性地全合成了天然黄酮碳苷Parkinsonin B.通过控制物质的量比,首先高选择性合成了2-羟基-4,6-二甲氧基苯乙酮(3),并与糖给体O-(2,3,4,6-四-O-苄基-α—D-葡萄糖基)三氯乙酰亚胺酯(7)发生立体专一性糖基化反应得到碳糖苷化合物8,化合物8经查耳酮路线进而合成黄酮碳苷Parkinsonin B(1).经IR,MS,^1H NMR及元素分析证实了产物及中间体的结构,同时讨论了全合成反应的主要影响因素,并对其^1H NMR解析进行了探讨.

英文摘要:

Owing to their special stability and prominent biological activity, C-glycosylflavones and their chemical synthesis have recently attracted considerable attention in the field of glycoscience. A total synthesis of glycosylflavone parkinsonin B with specific stereoselectivity is reported herein. 2-Hydroxy-4,6-bismethoxy acetophenone (3) was synthesized by one step in high regioselectivity under the optimal condition. The compound 3 was then glycosylated with O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl) trichloroacetimidate (7) as active glycosyl donor with specific stereoselectivity to produce compound 8. Parkinsonin B (1) was synthesized by the chalcone route from compound 8. The structures of target compound 1 and intermediates were confirmed by IR, MS, ^1H NMR spectra and element analysis.

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