methyl (3S,6R,7S,9R,E)-C6,C7-O-isopropilydene-3,6,7,9-tetrahydroxydodec-4-enoate C2,C9-O-bis-(R)-MTPA ester | 1190718-71-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (3S,6R,7S,9R,E)-C6,C7-O-isopropilydene-3,6,7,9-tetrahydroxydodec-4-enoate C2,C9-O-bis-(R)-MTPA ester
• CAS: 1190718-71-8
• 化学式: C₄₀H₅₀F₆O₁₀
• 分子量: 804.821
• InChiKey: ZJOPEZDWIPLVNZ-HJJRVHTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.41
• 重原子数：
  56.0
• 可旋转键数：
  20.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  115.82
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  achaetolide-II 在 吡啶 、 potassium carbonate 、 对甲苯磺酸 作用下， 反应 8.0h， 生成 methyl (3S,6R,7S,9R,E)-C6,C7-O-isopropilydene-3,6,7,9-tetrahydroxydodec-4-enoate C2,C9-O-bis-(R)-MTPA ester
  参考文献：
  名称：

  Achaetolide-II isolated from Helminthosporium velutinum TS28

  摘要：

  A C3-O-acylated analogue of achaetolide (2) was isolated from phytopathogenic fungus Helminthosporium velutinum TS28. The relative configuration involving the C3-O-acyl side chain was determined by NMR spectroscopic analysis combined with conformational analysis computer-assisted chemical shift calculations. The absolute configuration was established through ECD analysis after conversion into the dibenzoate (5). (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.08.013

文献信息

• Absolute stereochemistry and conformational analysis of achaetolide isolated from Ophiobolus sp.
  作者：Wilanfranco Caballero Tayone、Saori Shindo、Takanori Murakami、Masaru Hashimoto、Kazuaki Tanaka、Noboru Takada

  DOI：10.1016/j.tet.2009.07.005

  日期：2009.9

  Achaetolide, as reported by Bodo et al. in 1983, was isolated from a fermentation broth of Ophiobolus sp. We established the absolute stereochemistry of achaetolide to be 3S,6R,7S,9R by way of relative stereochemical assignment with H-1 NMR analyses employing the corresponding acetonide, determination of C3 and C9 stereochemistries by an extended Mosher method. (C) 2009 Elsevier Ltd. All rights reserved.