Selection of method for geometry optimization on neonicotinoid compounds

Wang, Huixian; Peng, Xin-lin; Jiang, Hua; Wang, Ling; Tao, Ya

doi:10.3724/sp.j.1238.2011.00693

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“…多甲氧基黄酮具有显著抗癌、抗炎等活性, 但其水溶性差, 对生物受体的亲和能力不强, 而进行糖基化后可大大改善上述缺点, 近年来对其化学全合成及其糖苷化的研究日益受到重视 [40] . 文献报道, 以相应甲氧基的苯乙酮和苯甲醛衍生物为原料, 通过 AFO 反应合成了一系列多氧甲基黄酮醇, 并以其中的 3',4',7-三甲氧基黄酮醇为苷元与不同的乙酰基保护的溴代糖进行糖苷缩合反应, 得到一系列以常见的单糖为糖基的 3',4',7-三甲氧基黄酮苷 [41] .…”

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Advances on Synthesis of Flavonoid Glycosides

Xu¹,

Li²,

Wu³

et al. 2019

Chin. J. Org. Chem.

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Flavonoid glycoside is commonly found in natural plants, possesses diverse bioactivities and potential medicinal values, and its synthesis methods are worthy to be studied. The synthesis of flavonoid glycosides covering the literatures from 2014 to 2018 is reviewed. The flavonoid glycoside synthesis includes two major methods of chemosynthesis and biosynthesis. Chemosynthesis includes total synthesis and semi-synthesis. The total synthesis has two classical methods of the Baker-Venkataraman (BK-VK) reaction and the Algar-Flynn-Oyamada (AFO) reaction. The semi-synthesis is usually starting from natural flavonoid, such as rutin, quercetin, kaempferol, naringenin and so on. Moreover, the chemosynthesis of flavonoid O-glucoside has three prime methods, Koening-Knorr method, phase transfer catalysis method, and glycosyl trichloroacetimidate method. As for the chemosynthesis of flavonoid C-glycoside, its glycosidic linkage is mainly completed via the O→C rearrangement reaction. Currently, the glycosyltransferase and glycosynthase are usually employed in the enzyme-catalyzed biosynthesis of flavonoid glycosides.

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“…柚皮苷和橙皮苷是天然二氢黄酮苷, 广泛分布于柑桔、柚子等芸香科属植物中. 文献报道, 柚皮苷和橙皮苷经过糖苷水解、碘/吡啶脱氢、甲基化或苄基保护、催化氢化脱苄基、糖基化等反应步骤, 得到了一系列多甲氧基黄酮苷 [40,46] . (30), 收率为 60% (Scheme 5).…”

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