(2S,3R,5Z,8R,9S)-8-[tert-butyl(diphenyl)silyl]oxy-9-ethyl-2-(hydroxymethyl)-2,3,4,7,8,9-hexahydrooxonin-3-ol | 140170-15-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2S,3R,5Z,8R,9S)-8-[tert-butyl(diphenyl)silyl]oxy-9-ethyl-2-(hydroxymethyl)-2,3,4,7,8,9-hexahydrooxonin-3-ol
• CAS: 140170-15-6；140225-14-5
• 化学式: C₂₇H₃₈O₄Si
• 分子量: 454.682
• InChiKey: ONTCQIAGFKXGNS-NZKTXEIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R,5Z,8R,9S)-8-[tert-butyl(diphenyl)silyl]oxy-9-ethyl-2-(hydroxymethyl)-2,3,4,7,8,9-hexahydrooxonin-3-ol 在 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 (Z,2S,3R,8R,9S)-8-tert-butyldiphenylsilanyloxy-9-ethyl-2-methansulfonyloxymethyl-3-(4-methoxybenzyloxy)-2,3,4,7,8,9-hexahydrooxonine
  参考文献：
  名称：

  A Synthesis of (+)-Obtusenyne

  摘要：

  报告利用克莱森重排和分子内水解作为关键步骤，合成了卤代中环醚天然产物(+)-obtusenyne。

  DOI：

  10.1055/s-2005-918470
• 作为产物：
  描述：

  (+/-)-(Z,3R,8R,9S)-3-tert-butyldimethylsilyloxy-8-tert-butyldiphenylsilanyloxy-9-ethyl-2-methylene-2,3,4,7,8,9-hexahydro-3H-oxonine 在 四丁基氟化铵 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,3R,5Z,8R,9S)-8-[tert-butyl(diphenyl)silyl]oxy-9-ethyl-2-(hydroxymethyl)-2,3,4,7,8,9-hexahydrooxonin-3-ol
  参考文献：
  名称：

  Studies towards the synthesis of obtusenyne. Synthesis of the hexahydrooxonin nucleus

  摘要：

  The advanced intermediate (the 2,3,4,7,8,9-hexahydrooxonin) 3 for the synthesis of the Laurencia oxonane natural product, obtusenyne 1 was prepared in 8 steps from the previously reported lactone 4. The key transformations were the stereoselective enolate hydroxylation of the lactone 4 and a hydroxyl-directed intramolecular hydrosilation of the enol ether 12.

  DOI：

  10.1016/s0040-4039(00)92339-6

文献信息

• Synthesis of (+)-Obtusenyne
  作者：S. Y. Frankie Mak、Neil R. Curtis、Andrew N. Payne、Miles S. Congreve、Andrew J. Wildsmith、Craig L. Francis、John E. Davies、Sofia I. Pascu、Jonathan W. Burton、Andrew B. Holmes

  DOI：10.1002/chem.200701567

  日期：2008.3.17

  An enantioselective synthesis of the halogenated medium-ring ether natural product (+)-obtusenyne is reported which uses the ring expansion of a seven-membered ketene acetal by means of a Claisen rearrangement to construct the core nine-membered oxygen heterocycle. The trans substituents across the ether linkage were established by using a transition-metal-catalyzed intramolecular hydrosilation reaction

  据报道，对卤化的中环醚天然产物（+）-ob烯炔的对映选择性合成是通过克莱森重排利用七元乙烯酮缩醛的扩环来构建核心的九元氧杂环。通过使用环外环烯醇醚的过渡金属催化的分子内硅氢化反应，建立了跨醚键的反式取代基。另外，据报道由2-脱氧-D-核糖正式合成对-奥布他汀。突出了有关中环氧杂环的化学反应的许多有趣的观点。
• An intramolecular hydrosilation approach to hexahydrooxonins related to obtusenyne. Effect of catalyst and conditions on stereoselectivity
  作者：Neil R. Curtis、Andrew B. Holmes

  DOI：10.1016/s0040-4039(00)92340-2

  日期：1992.1

  The intramolecular hydrosilation of the alpha-dialkysilyloxy enol ethers 3 and 5 followed by oxidative work-up resulted in the diastereoselective synthesis of either the hexahydrooxonin diol 7 or 8 according to the catalyst and conditions employed.
• A Synthesis of (+)-Obtusenyne
  作者：Jonathan W. Burton、Andrew B. Holmes、S. Y. Mak、Neil R. Curtis、Andrew N. Payne、Miles S. Congreve、Craig L. Francis

  DOI：10.1055/s-2005-918470

  日期：——

  A synthesis of the halogenated medium-ring ether natural product (+)-obtusenyne is reported utilizing a Claisen rearrangement and an intramolecular hydrosilation as key steps.

  报告利用克莱森重排和分子内水解作为关键步骤，合成了卤代中环醚天然产物(+)-obtusenyne。
• Studies towards the synthesis of obtusenyne. Synthesis of the hexahydrooxonin nucleus
  作者：Neil R. Curtis、Andrew B. Holmes、Mark G. Looney

  DOI：10.1016/s0040-4039(00)92339-6

  日期：1992.1

  The advanced intermediate (the 2,3,4,7,8,9-hexahydrooxonin) 3 for the synthesis of the Laurencia oxonane natural product, obtusenyne 1 was prepared in 8 steps from the previously reported lactone 4. The key transformations were the stereoselective enolate hydroxylation of the lactone 4 and a hydroxyl-directed intramolecular hydrosilation of the enol ether 12.