(2Z,4R,5R,6R,7R)-6-benzoyloxy-4-methyl-1,5-di-(tert-butyldimethylsiloxy)-7,8-di-(triethylsiloxy)oct-2-ene | 251319-66-1

• 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: (2Z,4R,5R,6R,7R)-6-benzoyloxy-4-methyl-1,5-di-(tert-butyldimethylsiloxy)-7,8-di-(triethylsiloxy)oct-2-ene
• 英文别名: [(Z,2R,3S,4R,5S)-4,8-bis[[tert-butyl(dimethyl)silyl]oxy]-5-methyl-1,2-bis(triethylsilyloxy)oct-6-en-3-yl] benzoate
• CAS: 251319-66-1
• 化学式: C₄₀H₇₈O₆Si₄
• 分子量: 767.398
• InChiKey: GJMADDDEOCKXIR-DRUQJRKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.23
• 重原子数：
  50
• 可旋转键数：
  25
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2Z,4R,5R,6R,7R)-6-benzoyloxy-4-methyl-1,5-di-(tert-butyldimethylsiloxy)-7,8-di-(triethylsiloxy)oct-2-ene 在 camphor-10-sulfonic acid 、 二甲基二环氧乙烷 、 potassium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 (2R,4aR,6R,7S,8R,8aR)-6-[(R)-1-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-8-(tert-butyl-dimethyl-silanyloxy)-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine
  参考文献：
  名称：

  Asymmetric synthesis of the F-pyran fragment of the altohyrtins

  摘要：

  The asymmetric synthesis of a differentially protected F-pyran ring of the altohyrtins has been achieved through an intramolecular cyclisation of a C-43 hydroxyl group onto a C-38-C-39 epoxide. Absolute stereochemistry was derived from an Evans boron aldol to control C-40 and C-41, the C-42-C-43 hydroxyl stereocentres from a Sharpless (-)-diethyl tartrate controlled epoxidation and the remaining stereocentres from substrate controlled diastereoselection. (C) 1999 Elsevier Science: Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01481-1
• 作为产物：
  描述：

  {(2R,3S)-3-[(Z)-(1R,2S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pent-3-enyl]-oxiranyl}-methanol 在 titanium(IV) isopropylate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (2Z,4R,5R,6R,7R)-6-benzoyloxy-4-methyl-1,5-di-(tert-butyldimethylsiloxy)-7,8-di-(triethylsiloxy)oct-2-ene
  参考文献：
  名称：

  Asymmetric synthesis of the F-pyran fragment of the altohyrtins

  摘要：

  The asymmetric synthesis of a differentially protected F-pyran ring of the altohyrtins has been achieved through an intramolecular cyclisation of a C-43 hydroxyl group onto a C-38-C-39 epoxide. Absolute stereochemistry was derived from an Evans boron aldol to control C-40 and C-41, the C-42-C-43 hydroxyl stereocentres from a Sharpless (-)-diethyl tartrate controlled epoxidation and the remaining stereocentres from substrate controlled diastereoselection. (C) 1999 Elsevier Science: Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01481-1

文献信息

• Asymmetric Epoxide Cyclisation Route to the F-pyran Fragment of the Altohyrtins and Key Aldol Studies
  作者：James C. Anderson、Benjamin P. McDermott、Edward J. Griffin

  DOI：10.1016/s0040-4020(00)00804-8

  日期：2000.10

  differentially protected F-pyran ring of the altohyrtins is described, which relies on a key intramolecular cyclisation of a C43 hydroxyl group onto a C38–C39 epoxide. The C38–C39 epoxide stereochemistry was achieved through optimisation of substrate control. Key aldol studies towards coupling the F-pyran ring with an E-pyran ring precursor was investigated, but unsuccessful.

  记载了高保护蛋白的差异保护的F-吡喃环的不对称合成过程，该过程依赖于C 43羟基在C 38 –C 39环氧化物上的关键分子内环化作用。C 38 –C 39环氧立体化学是通过优化底物控制来实现的。进行了有关将F-吡喃环与E-吡喃环前体偶联的关键羟醛研究，但未成功。
• Asymmetric synthesis of the F-pyran fragment of the altohyrtins
  作者：James C. Anderson、Benjamin P. McDermott

  DOI：10.1016/s0040-4039(99)01481-1

  日期：1999.9

  The asymmetric synthesis of a differentially protected F-pyran ring of the altohyrtins has been achieved through an intramolecular cyclisation of a C-43 hydroxyl group onto a C-38-C-39 epoxide. Absolute stereochemistry was derived from an Evans boron aldol to control C-40 and C-41, the C-42-C-43 hydroxyl stereocentres from a Sharpless (-)-diethyl tartrate controlled epoxidation and the remaining stereocentres from substrate controlled diastereoselection. (C) 1999 Elsevier Science: Ltd. All rights reserved.