ethyl (2R,3S)-2,3-dihydroxytridecanoate

• 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: ethyl (2R,3S)-2,3-dihydroxytridecanoate
• 化学式: C₁₅H₃₀O₄
• 分子量: 274.401
• InChiKey: CPAXBQDXTARHEU-UONOGXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (2R,3S)-2,3-dihydroxytridecanoate 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以95%的产率得到ethyl (2R,3S)-2,3-(isopropylidenedioxy)tridecanoate
  参考文献：
  名称：

  Total Syntheses of Schulzeines B and C

  摘要：

  Schulzeines B (2) and C (3) were synthesized by a convergent strategy using epimeric tricyclic lactam building blocks, 4 and 5, and the C28 fatty acid side chain 6. Syntheses of tricyclic lactams (4/5) were achieved by Bischler-Napieralski reaction. Sharpless asymmetric dihy-droxylation and BINAL-H-mediated asymmetric reduction of an enone was employed to prepare the key fatty acid side chain 6. The spectral as well as analytical data of 2 and 3 were in good agreement with the reported data for the natural products, thus confirming their assigned structures.

  DOI：

  10.1021/jo070560h
• 作为产物：
  描述：

  乙基十三碳-2-烯酸酯 在 potassium osmate(VI) 、 potassium hexacyanoferrate(III) Hydroquinone 1,4-phthalazinediyl diether 、 甲基磺酰胺 、 potassium carbonate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 6.0h， 以85%的产率得到ethyl (2R,3S)-2,3-dihydroxytridecanoate
  参考文献：
  名称：

  Total Syntheses of Schulzeines B and C

  摘要：

  Schulzeines B (2) and C (3) were synthesized by a convergent strategy using epimeric tricyclic lactam building blocks, 4 and 5, and the C28 fatty acid side chain 6. Syntheses of tricyclic lactams (4/5) were achieved by Bischler-Napieralski reaction. Sharpless asymmetric dihy-droxylation and BINAL-H-mediated asymmetric reduction of an enone was employed to prepare the key fatty acid side chain 6. The spectral as well as analytical data of 2 and 3 were in good agreement with the reported data for the natural products, thus confirming their assigned structures.

  DOI：

  10.1021/jo070560h

文献信息

• Diastereoselective synthesis of (+)-nephrosterinic acid and (+)-protolichesterinic acid
  作者：Rodney A. Fernandes、Mahesh B. Halle、Asim K. Chowdhury、Arun B. Ingle

  DOI：10.1016/j.tetasy.2011.12.012

  日期：2012.1

  A diastereoselective synthesis of (+)-nephrosterinic acid and (+)-protolichesterinic acid, common members of the paraconic acids is described. The synthesis is based on a diastereoselective orthoester Johnson-Claisen rearrangement of a (Z)-allyl alcohol with a vicinal dioxolane moiety as key steps. The synthesis is completed in 10 steps and with overall yields of 15.9% for (+)-nephrosterinic acid and 16.4% for (+)-protolichesterinic acid. (C) 2012 Elsevier Ltd. All rights reserved.