dibenzyl (-)-(2R,3R)-2,3-bis{3-[2,3-bis(3,4-dibenzyloxy)phenyl]prop-2-enoyloxy}-L-tartrate | 488148-82-9

• 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: dibenzyl (-)-(2R,3R)-2,3-bis{3-[2,3-bis(3,4-dibenzyloxy)phenyl]prop-2-enoyloxy}-L-tartrate
• 英文别名: dibenzyl (2R,3R)-2,3-bis[[(E)-3-[3,4-bis(phenylmethoxy)phenyl]prop-2-enoyl]oxy]butanedioate
• CAS: 488148-82-9
• 化学式: C₆₄H₅₄O₁₂
• 分子量: 1015.13
• InChiKey: WYUQNYOJZSKCGH-IULKUNFESA-N

物化性质

• 沸点：
  45-47 °C
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.9
• 重原子数：
  76
• 可旋转键数：
  29
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  dibenzyl (-)-(2R,3R)-2,3-bis{3-[2,3-bis(3,4-dibenzyloxy)phenyl]prop-2-enoyloxy}-L-tartrate 在 三乙基硅烷 、 palladium diacetate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到菊苣酸
  参考文献：
  名称：

  A Convenient Synthesis of the Echinacea-Derived Immunostimulator and HIV-1 Integrase Inhibitor (−)-(2R,3R)-Chicoric Acid

  摘要：

  The Echinacea-derived immunostimulator and HIV-1 integrase inhibitor (-)-chicoric acid (=2,3-bis([3(3,4-dihydroxyphenyl)-1-oxoprop-2-enyl]oxy)butanedioic acid; 1a) was conveniently prepared via a silane-promoted Pd-mediated chemoselective hydrogenolysis of its perbenzylated derivative 12a, which was generated from an efficient and reliable carbodiimide-mediated coupling reaction between the caffeic acid dibenzyl ether derivative 7 and commercially available (+)-dibenzyl L-tartrate (9a). The other naturally occurring dextrorotatory chicoric acid (1b) can be similarly prepared.

  DOI：

  10.1002/1522-2675(200208)85:8<2328::aid-hlca2328>3.0.co;2-x
• 作为产物：
  描述：

  TRANS-咖啡酸 在 4-二甲氨基吡啶 、 氢氧化钾 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 乙酰氯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 112.0h， 生成 dibenzyl (-)-(2R,3R)-2,3-bis{3-[2,3-bis(3,4-dibenzyloxy)phenyl]prop-2-enoyloxy}-L-tartrate
  参考文献：
  名称：

  A Convenient Synthesis of the Echinacea-Derived Immunostimulator and HIV-1 Integrase Inhibitor (−)-(2R,3R)-Chicoric Acid

  摘要：

  The Echinacea-derived immunostimulator and HIV-1 integrase inhibitor (-)-chicoric acid (=2,3-bis([3(3,4-dihydroxyphenyl)-1-oxoprop-2-enyl]oxy)butanedioic acid; 1a) was conveniently prepared via a silane-promoted Pd-mediated chemoselective hydrogenolysis of its perbenzylated derivative 12a, which was generated from an efficient and reliable carbodiimide-mediated coupling reaction between the caffeic acid dibenzyl ether derivative 7 and commercially available (+)-dibenzyl L-tartrate (9a). The other naturally occurring dextrorotatory chicoric acid (1b) can be similarly prepared.

  DOI：

  10.1002/1522-2675(200208)85:8<2328::aid-hlca2328>3.0.co;2-x

文献信息

• A Convenient Synthesis of the Echinacea-Derived Immunostimulator and HIV-1 Integrase Inhibitor (−)-(2R,3R)-Chicoric Acid
  作者：Anne-Marie Lamidey、Lionel Fernon、Laurent Pouységu、Charlotte Delattre、Stéphane Quideau、Patrick Pardon

  DOI：10.1002/1522-2675(200208)85:8<2328::aid-hlca2328>3.0.co;2-x

  日期：2002.8

  The Echinacea-derived immunostimulator and HIV-1 integrase inhibitor (-)-chicoric acid (=2,3-bis([3(3,4-dihydroxyphenyl)-1-oxoprop-2-enyl]oxy)butanedioic acid; 1a) was conveniently prepared via a silane-promoted Pd-mediated chemoselective hydrogenolysis of its perbenzylated derivative 12a, which was generated from an efficient and reliable carbodiimide-mediated coupling reaction between the caffeic acid dibenzyl ether derivative 7 and commercially available (+)-dibenzyl L-tartrate (9a). The other naturally occurring dextrorotatory chicoric acid (1b) can be similarly prepared.