11(R),12(S),15(S)-trihydroxyeicosa-5(Z),8(Z),13(E)-trienoic acid | 849797-52-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 11(R),12(S),15(S)-trihydroxyeicosa-5(Z),8(Z),13(E)-trienoic acid
• 英文别名: (5Z,8Z,11R,12S,13E,15S)-11,12,15-trihydroxyicosa-5,8,13-trienoic acid
• CAS: 849797-52-0
• 化学式: C₂₀H₃₄O₅
• 分子量: 354.487
• InChiKey: PRMWQIVYOYCJQC-BUWRLEMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 11(R),12(S),15(S)-trihydroxyeicosa-5(Z),8(Z),13(E)-trienoic acid 生成 11(R),12(S),15(S)-trihydroxyeicosatrienoic acid
  参考文献：
  名称：

  Asymmetric synthesis of the stereoisomers of 11,12,15(S)-trihydroxyeicosa-5(Z),8(Z),13(E)-trienoic acid, a potent endothelium-derived vasodilator

  摘要：

  The four stereoisomers of the endothelial-derived vasorelaxant 11,12,15(S)-trihydroxyeicosatrienoic acid [1, 11,12,15(S)THETA] were prepared by a triply convergent, asymmetric route that exploited the stereospecific, copper mediated cross-coupling of alpha,beta-dialkoxystannanes with organic electrophiles and the utility of dialkylthionocarbarnates as orthogonal alcohol protective groups. Only 11(R),12(S),15(S)-THETA was comparable to natural material by HPLC, GC/MS, and in vitro bioassay. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.019
• 作为产物：
  描述：

  10-hydroxy-deca-5,8-diynoic acid methyl ester 在 镍 chromium dichloride 、 sodium hydroxide 、 sodium periodate 、 氢气 、 双氧水 、 三溴化磷 、 溶剂黄146 、 nickel dichloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， -10.0~50.0 ℃ 、101.33 kPa 条件下， 反应 52.0h， 生成 11(R),12(S),15(S)-trihydroxyeicosa-5(Z),8(Z),13(E)-trienoic acid
  参考文献：
  名称：

  Asymmetric synthesis of the stereoisomers of 11,12,15(S)-trihydroxyeicosa-5(Z),8(Z),13(E)-trienoic acid, a potent endothelium-derived vasodilator

  摘要：

  The four stereoisomers of the endothelial-derived vasorelaxant 11,12,15(S)-trihydroxyeicosatrienoic acid [1, 11,12,15(S)THETA] were prepared by a triply convergent, asymmetric route that exploited the stereospecific, copper mediated cross-coupling of alpha,beta-dialkoxystannanes with organic electrophiles and the utility of dialkylthionocarbarnates as orthogonal alcohol protective groups. Only 11(R),12(S),15(S)-THETA was comparable to natural material by HPLC, GC/MS, and in vitro bioassay. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.019

文献信息

• Allylic Alcohol Transposition by Ortho Ester-Initiated Carbonate Extension. Synthesis of the Vasodilator 11(<i>R</i>),12(<i>S</i>),15(<i>S</i>)-Trihydroxyeicosa- 5(<i>Z</i>),8(<i>Z</i>),13(<i>E</i>)-trienoic Acid
  作者：Raymond E. Conrow

  DOI：10.1021/ol0608808

  日期：2006.5.1

  [reaction: see text] The title compound 1 was obtained via methyl ester 2, which was synthesized in four steps from an isomeric 11,14,15-triol ester 5. In the key step, Boc orthoformate 9 was treated with TMS triflate to initiate intramolecular nucleophilic substitution with allylic transposition, forming cyclic carbonates 10 and 11.

  [反应：见正文]标题化合物1是通过甲酯2获得的，该甲酯是由11、14、15-三醇酯5的异构体通过四个步骤合成的。在关键步骤中，用三氟甲磺酸TMS处理原甲酸Boc 9用烯丙基转座引发分子内亲核取代，形成环状碳酸酯10和11。