(R)-methyl 2-acetoxy-3-(3,4-diacetoxyphenyl)propanoate | 1162198-76-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-methyl 2-acetoxy-3-(3,4-diacetoxyphenyl)propanoate
• 英文别名: (+)-(R)-methyl 3-[3,4-bis(acetoxy)phenyl]-2-acetoxypropanoate；methyl (2R)-2-acetyloxy-3-(3,4-diacetyloxyphenyl)propanoate
• CAS: 1162198-76-6
• 化学式: C₁₆H₁₈O₈
• 分子量: 338.314
• InChiKey: GICBCXVRCZFBEW-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl 3-[3,4-bis(tertbutyldimethylsilyloxy)phenyl]propenoate 在 吡啶 、 三乙基硅烷 、 甲基磺酰胺 、 AD-mix-α 、 三氟化硼乙醚 、 水 、 triethylamine tris(hydrogen fluoride) 作用下， 以 吡啶 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 62.5h， 生成 (R)-methyl 2-acetoxy-3-(3,4-diacetoxyphenyl)propanoate
  参考文献：
  名称：

  Oresbiusins A 和 B、它们的对映体和外消旋体的首次全合成：构型修正和抗 HIV 活性

  摘要：

  (+)-、(-)-和(±)-形式的oresbiusin A的第一次全合成分五个步骤完成，总产率为约。70%。具有光学活性的关键中间体是通过 Sharpless 不对称二羟基化反应生成的。这些努力使我们能够建立这种具有右旋和 2S 构型的天然产物的绝对构型。此外，oresbiusin B 的两种对映异构体及其外消旋体的总合成分六个步骤完成，总产率为 58%。在这些化合物中，发现具有左旋旋转的非天然 oresbiusin A 在 H9 细胞中具有剂量依赖性的抗 HIV-1 活性，而其他化合物则无活性。

  DOI：

  10.1002/ejoc.201200689

文献信息

• Asymmetric synthesis and biological evaluation of Danshensu derivatives as anti-myocardial ischemia drug candidates
  作者：Cunnan Dong、Yang Wang、Yi Zhun Zhu

  DOI：10.1016/j.bmc.2009.02.065

  日期：2009.5

  The synthesis and bioactivities of Danshensu derivatives (R)-methyl 2-acetoxy-3-(3,4-diacetoxyphenyl) propanoate (1a), (R)-methyl 2-acetoxy-3-(3,4-methylenedioxyphenyl) propanoate (1b) and their racemates 7 and 10 were reported in this paper. These derivatives were designed to improve their chemical stability and liposolubility by protecting Danshensu's phenolic hydroxyl groups with acetyl or methylene which could be readily hydrolyzed to release bioactive Danshensu. The asymmetric synthesis of 1a and 1b were achieved by catalytic hydrogenation of (Z)-methyl 2-acetoxy-3-(3,4-diacetoxyphenyl)-2-propenoate (6a) and (Z)-methyl 2-acetoxy-3-(3,4-methylenedioxyphenyl)-2-propenoate (6b) in excellent enantiomeric excesses (92% ee and 98% ee, respectively) and good yields (>89%). An unexpected intermediate product, (Z)-2-acetoxy-3-(3,4-dihydroxyphenyl) acrylic acid (4c) was obtained with high chemoselectivity in 86% yield by keeping the reaction temperature at 60 degrees C and its structure was identified by Xray single crystal diffraction analysis. 1a, 1b and their racemates 7, 10 as well as 4c exhibited potent protective activities against hypoxia-induced cellular damage. The in vitro test showed that all these compounds could increase cell viability, and inhibit lipid hyperoxidation. Furthermore, 1a and 4c could inhibit apoptosis by regulating the expression of apoptosis-related molecule in gene and protein levels, up-regulating the expression of bcl-2 and down-regulating bax and caspase-3. The in vivo test indicated that 4c exhibited anti-myocardial ischemic effects featured by reducing infarction size and increasing the level of the intracellular enzymes detectable in serum. Therefore, these Danshensu derivatives may be good drug candidates for anti-myocardial ischemia therapy and merit further investigation. (C) 2009 Elsevier Ltd. All rights reserved.
• First Total Syntheses of Oresbiusins A and B, Their Antipodes, and Racemates: Configuration Revision and Anti-HIV Activity
  作者：Jih Ru Hwu、Tirumala G. Varadaraju、Ibrahim S. Abd-Elazem、Ru Chih C. Huang

  DOI：10.1002/ejoc.201200689

  日期：2012.9

  The first total syntheses of oresbiusin A in the (+)-, (–)-, and (±)-forms were accomplished in five steps with overall yields of ca. 70 %. The key intermediates with optical activity were generated through a Sharpless asymmetric dihydroxylation reaction. These efforts allowed us to establish the absolute configuration of this natural product with dextrorotary and a 2S configuration. In addition, the

  (+)-、(-)-和(±)-形式的oresbiusin A的第一次全合成分五个步骤完成，总产率为约。70%。具有光学活性的关键中间体是通过 Sharpless 不对称二羟基化反应生成的。这些努力使我们能够建立这种具有右旋和 2S 构型的天然产物的绝对构型。此外，oresbiusin B 的两种对映异构体及其外消旋体的总合成分六个步骤完成，总产率为 58%。在这些化合物中，发现具有左旋旋转的非天然 oresbiusin A 在 H9 细胞中具有剂量依赖性的抗 HIV-1 活性，而其他化合物则无活性。