(3aR,3bS,5aS,6S,8aS,8bS,10R,10aS)-10-[tert-butyl(dimethyl)silyl]oxy-10a-[(1R)-2-hydroxy-1-(methoxymethoxy)ethyl]-6-(methoxymethoxy)-3a,5a-dimethyl-3b,4,5,6,7,8,8a,8b,9,10-decahydro-3H-indeno[5,4-e][1]benzofuran-2-one | 1252819-86-5

• 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: (3aR,3bS,5aS,6S,8aS,8bS,10R,10aS)-10-[tert-butyl(dimethyl)silyl]oxy-10a-[(1R)-2-hydroxy-1-(methoxymethoxy)ethyl]-6-(methoxymethoxy)-3a,5a-dimethyl-3b,4,5,6,7,8,8a,8b,9,10-decahydro-3H-indeno[5,4-e][1]benzofuran-2-one
• CAS: 1252819-86-5
• 化学式: C₂₉H₅₂O₈Si
• 分子量: 556.813
• InChiKey: GXBIPTPUYCMXPR-JDXBSJTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  [(1S,2R,4S,5S,8S,9S,12S,13R,15S,17R,18S)-2-[tert-butyl(dimethyl)silyl]oxy-8,18-bis(methoxymethoxy)-9,13-dimethyl-16,19-dioxapentacyclo[13.3.1.01,13.04,12.05,9]nonadecan-17-yl] acetate 在 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以86%的产率得到(3aR,3bS,5aS,6S,8aS,8bS,10R,10aS)-10-[tert-butyl(dimethyl)silyl]oxy-10a-[(1R)-2-hydroxy-1-(methoxymethoxy)ethyl]-6-(methoxymethoxy)-3a,5a-dimethyl-3b,4,5,6,7,8,8a,8b,9,10-decahydro-3H-indeno[5,4-e][1]benzofuran-2-one
  参考文献：
  名称：

  高度取代和立体定义的顺式稠合内酯的高效构建

  摘要：

  本文描述的方法涉及环状烯-缩醛的环氧化反应，以自发生成 6α-羟基-双-缩醛，可作为 Cannizzaro 型重排的前体，产生双角取代的顺式稠合内酯。氧化剂，m-CPBA 或 NaBO 3 ，以及取代模式在确定环氧化/开环顺序的过程中都很重要，NaBO 3 是环氧化/自发开环/环的理想亲电氧化剂-系统交换序列。

  DOI：

  10.1002/ejoc.201000556

文献信息

• Synthesis of nor-sesquiterpene spirolactones and their steroidal hybrids revisited. The neopentyl dilemma: misassignment of one stereocentre may necessitate a completely new approach
  作者：Imad Safir、Angeline Chanu、Zobida Elkhayat、Ramkrishna Basak、Siméon Arseniyadis

  DOI：10.1016/j.tetasy.2014.08.005

  日期：2014.10

  Inversion at the highly congested Cl position of 1-epi-pathylactone A (1-epi-1), or its corresponding steroidal hybrid 8a, using a diverse range of published procedures including microwave assisted Mitsunobu reaction or via oxidation to the corresponding ketone and subsequent reduction, was unsuccessful in our hands. Attempts to convert the Cl hydroxyl group into its corresponding chloride, en route to napalilactone 2a, also failed. Precursors with the Cl cc configuration installed at early stage proved not to be amenable to the targets under a broad range of conditions. (C) 2014 Elsevier Ltd. All rights reserved.
• Efficient Construction of Highly Substituted and Stereodefined cis-Fused Lactones
  作者：Zobida Elkhayat、Imad Safir、Zoila Gandara、Pascal Retailleau、Siméon Arseniyadis

  DOI：10.1002/ejoc.201000556

  日期：2010.9

  ene-acetals to spontaneously generate 6α-hydroxy-bis-acetals that could serve as precursors for a Cannizzaro-type rearrangement, yielding bis-angularly substituted cis-fused lactones. Both the oxidizing reagent, m-CPBA or NaBO 3 , and the substitution pattern can be important in determining the course of the epoxidation/ring-opening sequence, with NaBO 3 being the ideal electrophilic oxidant for the

  本文描述的方法涉及环状烯-缩醛的环氧化反应，以自发生成 6α-羟基-双-缩醛，可作为 Cannizzaro 型重排的前体，产生双角取代的顺式稠合内酯。氧化剂，m-CPBA 或 NaBO 3 ，以及取代模式在确定环氧化/开环顺序的过程中都很重要，NaBO 3 是环氧化/自发开环/环的理想亲电氧化剂-系统交换序列。