3-O-β-D-glucopyranosyl-7-hydroxy-9-methoxy-1-methyl-6H-dibenzo[b,d]pyran-6-one | 1422465-59-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-β-D-glucopyranosyl-7-hydroxy-9-methoxy-1-methyl-6H-dibenzo[b,d]pyran-6-one
• 英文别名: 3-O-β-D-glucopyranosylalternariol 9-O-methyl ether；3-O-β-D-glucopyranosyl-9-O-methylalternariol；AME-3-β,D-glucoside；lysilactone A；7-hydroxy-9-methoxy-1-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzo[c]chromen-6-one
• CAS: 1422465-59-5
• 化学式: C₂₁H₂₂O₁₀
• 分子量: 434.4
• InChiKey: UXFHGJBARUQTBN-FKRBRYKNSA-N

物化性质

• 沸点：
  767.7±60.0 °C(Predicted)
• 密度：
  1.554±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  155
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  5-hydroxy-7-methoxy-2,2-dimethyl-benzo[1,3]dioxin-4-one 在 2-双环己基膦-2',6'-二甲氧基联苯 、 吡啶 、 四(三苯基膦)钯 、 四丁基溴化铵 、 sodium methylate 、 palladium diacetate 、 potassium carbonate 、 caesium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 氯仿 、 水 为溶剂， 反应 25.0h， 生成 3-O-β-D-glucopyranosyl-7-hydroxy-9-methoxy-1-methyl-6H-dibenzo[b,d]pyran-6-one
  参考文献：
  名称：

  Lysilactones A-C，3个6 ħ -二苯并[ b，d ]吡喃从-6-酮糖苷珍珠菜，Lysilactone A的全合成

  摘要：

  三6 ħ -二苯并[ B，d ]吡喃-6-酮命名lysilactones A-C（糖苷1 - 3）购自的地上部分分离珍珠菜。使用光谱分析和化学证据阐明了它们的结构。这是6 H-二苯并[ b，d ]吡喃-6-糖苷的首次报道。此外，我们已经完成了莱西内酯A的全合成。关键步骤是用于构建中央联芳基键的Suzuki偶联。从间苯二糖酸和大黄酚开始，分八步制备了Lysilactone A，最长的线性序列为七步。

  DOI：

  10.1016/j.tet.2013.01.029

文献信息

• Total synthesis of masked Alternaria mycotoxins—sulfates and glucosides of alternariol (AOH) and alternariol-9-methyl ether (AME)
  作者：Hannes Mikula、Philipp Skrinjar、Barbara Sohr、Doris Ellmer、Christian Hametner、Johannes Fröhlich

  DOI：10.1016/j.tet.2013.10.008

  日期：2013.12

  The synthesis of different protected alternariol derivatives using intramolecular cyclization of iodoresorcylic acid phenyl esters by palladium-catalyzed C-H activation as key step is presented. Furthermore, chemical sulfation and glucosylation were applied for the preparation of conjugated Alternaria mycotoxins. These compounds are suspected to be formed during metabolism in contaminated plants. Therefore, all synthetic conjugates prepared within this work serve as reference materials for further studies in the fields of bioanalytics and toxicology of mycotoxins. (C) 2013 Elsevier Ltd. All rights reserved.
• Lysilactones A–C, three 6H-dibenzo[b,d]pyran-6-one glycosides from Lysimachia clethroides, total synthesis of Lysilactone A
  作者：Dong Liang、Huan Luo、Yan-Fei Liu、Zhi-You Hao、Yan Wang、Chun-Lei Zhang、Qing-Jian Zhang、Ruo-Yun Chen、De-Quan Yu

  DOI：10.1016/j.tet.2013.01.029

  日期：2013.3

  Three 6H-dibenzo[b,d]pyran-6-one glycosides named lysilactones A–C (1–3) were isolated from the aerial parts of Lysimachia clethroides. Their structures were elucidated using spectroscopic analysis and chemical evidence. This is the first report of 6H-dibenzo[b,d]pyran-6-one glycosides. Furthermore, we have finished a total synthesis of lysilactone A. The key step is a Suzuki coupling used for the

  三6 ħ -二苯并[ B，d ]吡喃-6-酮命名lysilactones A-C（糖苷1 - 3）购自的地上部分分离珍珠菜。使用光谱分析和化学证据阐明了它们的结构。这是6 H-二苯并[ b，d ]吡喃-6-糖苷的首次报道。此外，我们已经完成了莱西内酯A的全合成。关键步骤是用于构建中央联芳基键的Suzuki偶联。从间苯二糖酸和大黄酚开始，分八步制备了Lysilactone A，最长的线性序列为七步。