(2S,3R,4R,4aR,8R,8aR)-2,3,4-tris((tert-butyldimethylsilyl)oxy)-8a-(phenylsulfonyl)-8-((trimethylsilyl)oxy)-3,4,4a,5,8,8a-hexahydronaphthalen-1(2H)-one | 1354784-79-4

• 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: (2S,3R,4R,4aR,8R,8aR)-2,3,4-tris((tert-butyldimethylsilyl)oxy)-8a-(phenylsulfonyl)-8-((trimethylsilyl)oxy)-3,4,4a,5,8,8a-hexahydronaphthalen-1(2H)-one
• CAS: 1354784-79-4
• 化学式: C₃₇H₆₈O₇SSi₄
• 分子量: 769.351
• InChiKey: KRJNQTMOFWZMQS-SNFBGZBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.75
• 重原子数：
  49.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,4aR,8R,8aR)-2,3,4-tris((tert-butyldimethylsilyl)oxy)-8a-(phenylsulfonyl)-8-((trimethylsilyl)oxy)-3,4,4a,5,8,8a-hexahydronaphthalen-1(2H)-one 在 2,6-二甲基吡啶 、 Jones reagent 、 samarium diiodide 、 四氯化锡 、 三乙酰氧基硼氢化钠 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 二甲基亚砜 、 1,2-二氯乙烷 、 丙酮 、 甲苯 为溶剂， 反应 99.67h， 生成 (1S,2S,3R,4S,4aR,8aS)-1-allyl-2,3-bis((tert-butyldimethylsilyl)oxy)-4,8,8a-tris((trimethylsilyl)oxy)-1,2,3,4,4a,8a-hexahydronaphthalen-1-ol
  参考文献：
  名称：

  The first total synthesis of hibarimicinone, a potent v-Src tyrosine kinase inhibitor

  摘要：

  The first total synthesis of hibarimicinone has been achieved. The polyhydroxydecalin moieties (AB and GH rings) have been synthesized from sulfonylenone 4 derived from D-arabinose. The chiral biaryl 20 was coupled with two polyhydroxydecalins 11 by Michael-Dieckmann type condensation to give the eight rings system. Aromatization and oxidation with Ag+ gave quinone 24, and the subsequential transannular etheration gave the hibarimicinone skeleton. Deprotection and tautomerization were performed in one pot to give hibarimicinone (1). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.062
• 作为产物：
  描述：

  1-(trimethylsiloxy)-1,3-butadiene 、 (4R,5R,6S)-2-(benzenesulfonyl)-4,5,6-tris[[tert-butyl(dimethyl)silyl]oxy]cyclohex-2-en-1-one 在 DTBC 作用下， 以 甲苯 为溶剂， 反应 96.0h， 以90%的产率得到(2S,3R,4R,4aR,8R,8aR)-2,3,4-tris((tert-butyldimethylsilyl)oxy)-8a-(phenylsulfonyl)-8-((trimethylsilyl)oxy)-3,4,4a,5,8,8a-hexahydronaphthalen-1(2H)-one
  参考文献：
  名称：

  The first total synthesis of hibarimicinone, a potent v-Src tyrosine kinase inhibitor

  摘要：

  The first total synthesis of hibarimicinone has been achieved. The polyhydroxydecalin moieties (AB and GH rings) have been synthesized from sulfonylenone 4 derived from D-arabinose. The chiral biaryl 20 was coupled with two polyhydroxydecalins 11 by Michael-Dieckmann type condensation to give the eight rings system. Aromatization and oxidation with Ag+ gave quinone 24, and the subsequential transannular etheration gave the hibarimicinone skeleton. Deprotection and tautomerization were performed in one pot to give hibarimicinone (1). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.062