methyl (5Z,8R)-8-[(tert-butyldimethylsilyl)oxy]-9-hydroxy-5-nonenoate | 1610421-79-8

• 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: methyl (5Z,8R)-8-[(tert-butyldimethylsilyl)oxy]-9-hydroxy-5-nonenoate
• CAS: 1610421-79-8
• 化学式: C₁₆H₃₂O₄Si
• 分子量: 316.513
• InChiKey: FUEKBYJEEXLRCL-IUCKJTJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  21.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (5Z,8R)-8-[(tert-butyldimethylsilyl)oxy]-9-hydroxy-5-nonenoate 在 六甲基磷酰三胺 、 草酰氯 、 cerium(III) chloride heptahydrate 、 sodium hexamethyldisilazane 、 二甲基亚砜 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 4.08h， 生成 methyl (5Z,8R,9E,11S,12S,14Z)-8-(tert-butyldimethylsilyl)oxy-11-methoxy-12-(4-methoxyphenyl)methoxy-5,9,14-icosatrienoate
  参考文献：
  名称：

  Synthesis of topsentolides A2 and C2, and non-enzymatic conversion of the former to the latter

  摘要：

  The first total synthesis of the marine-derived cytotoxin topsentolide A(2), which eventually culminated in its stereochemical determination, was accomplished in 17 steps from a known chiral alcohol. An improved synthesis of its congener, topsentolide C-2, from a synthetic intermediate of topsentolide A(2) was also performed by utilizing the Yamaguchi lactonization to construct its nine-membered lactone ring. Treatment of epoxide ring-containing topsentolide Ay with HCl/MeOH brought about its quantitative conversion into topsentolide C-2. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.040
• 作为产物：
  描述：

  methyl (5Z,8R)-8,9-bis[(tert-butyldimethylsilyl)oxy]-5-nonenoate 在 氟化氢吡啶 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 24.0h， 以70%的产率得到methyl (5Z,8R)-8-[(tert-butyldimethylsilyl)oxy]-9-hydroxy-5-nonenoate
  参考文献：
  名称：

  Synthesis of topsentolides A2 and C2, and non-enzymatic conversion of the former to the latter

  摘要：

  The first total synthesis of the marine-derived cytotoxin topsentolide A(2), which eventually culminated in its stereochemical determination, was accomplished in 17 steps from a known chiral alcohol. An improved synthesis of its congener, topsentolide C-2, from a synthetic intermediate of topsentolide A(2) was also performed by utilizing the Yamaguchi lactonization to construct its nine-membered lactone ring. Treatment of epoxide ring-containing topsentolide Ay with HCl/MeOH brought about its quantitative conversion into topsentolide C-2. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.040