[4-[Tert-butyl(dimethyl)silyl]oxy-5-[7-[tert-butyl(dimethyl)silyl]oxy-4-hydroxyhept-1-en-5-yn-2-yl]-2-methyl-3-phenylmethoxyphenyl] 4-methylbenzenesulfonate | 924888-10-8

• 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: [4-[Tert-butyl(dimethyl)silyl]oxy-5-[7-[tert-butyl(dimethyl)silyl]oxy-4-hydroxyhept-1-en-5-yn-2-yl]-2-methyl-3-phenylmethoxyphenyl] 4-methylbenzenesulfonate
• CAS: 924888-10-8
• 化学式: C₄₀H₅₆O₇SSi₂
• 分子量: 737.117
• InChiKey: BCKJDKJTXDBNSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.82
• 重原子数：
  50
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  99.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [4-[Tert-butyl(dimethyl)silyl]oxy-5-[7-[tert-butyl(dimethyl)silyl]oxy-4-hydroxyhept-1-en-5-yn-2-yl]-2-methyl-3-phenylmethoxyphenyl] 4-methylbenzenesulfonate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Multiple chirality transfers in the enantioselective synthesis of 11-O-debenzoyltashironin. Chiroptical analysis of the key cascade

  摘要：

  The mechanism of the cascade oxidative dearomatization-transannular Diels-Alder was investigated in the context of an asymmetric route to (-)-11-O-debenzoyltashironin. Although the oxidative dearomatization provides two acetal intermediates, the transannular Diels-Alder proceeds spontaneously from only one of the acetal isomers. Access to enantioenriched tetracyclic adduct was gained through the use of optically active allene. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.07.139
• 作为产物：
  描述：

  2,6-二羟基甲苯 在 tris(dibenzylideneacetone)dipalladium (0) 盐酸 、 甲醇 、 N-bromosuccinamide 、 三叔丁基膦 、 TEA 、 diethylzinc 、 四丁基碘化铵 、 potassium carbonate 、 戴斯-马丁氧化剂 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 22.17h， 生成 [4-[Tert-butyl(dimethyl)silyl]oxy-5-[7-[tert-butyl(dimethyl)silyl]oxy-4-hydroxyhept-1-en-5-yn-2-yl]-2-methyl-3-phenylmethoxyphenyl] 4-methylbenzenesulfonate
  参考文献：
  名称：

  The Total Synthesis of (±)-11-O-Debenzoyltashironin

  摘要：

  The total synthesis of the putative non-peptidyl neurotrophic factor 11-O-debenzoyltashironin has been accomplished. The key transformation involves a biomimetic oxidative dearomatization/transannular Diels-Alder sequence that closes the tetracyclic carbon skeleton present in the natural product.

  DOI：

  10.1021/ja0670254

文献信息

• The Total Synthesis of (±)-11-<i>O</i>-Debenzoyltashironin
  作者：Silas P. Cook、Alessandra Polara、Samuel J. Danishefsky

  DOI：10.1021/ja0670254

  日期：2006.12.1

  The total synthesis of the putative non-peptidyl neurotrophic factor 11-O-debenzoyltashironin has been accomplished. The key transformation involves a biomimetic oxidative dearomatization/transannular Diels-Alder sequence that closes the tetracyclic carbon skeleton present in the natural product.
• Multiple chirality transfers in the enantioselective synthesis of 11-O-debenzoyltashironin. Chiroptical analysis of the key cascade
  作者：Alessandra Polara、Silas P. Cook、Samuel J. Danishefsky

  DOI：10.1016/j.tetlet.2008.07.139

  日期：2008.10

  The mechanism of the cascade oxidative dearomatization-transannular Diels-Alder was investigated in the context of an asymmetric route to (-)-11-O-debenzoyltashironin. Although the oxidative dearomatization provides two acetal intermediates, the transannular Diels-Alder proceeds spontaneously from only one of the acetal isomers. Access to enantioenriched tetracyclic adduct was gained through the use of optically active allene. (C) 2008 Elsevier Ltd. All rights reserved.