(2S,3R,6Z,9R)-3-[tert-butyl(dimethyl)silyl]oxy-7-methyl-9-(phenylmethoxymethyl)-2,3,4,5,8,9-hexahydrooxonine-2-carbaldehyde | 958461-32-0

• 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,6Z,9R)-3-[tert-butyl(dimethyl)silyl]oxy-7-methyl-9-(phenylmethoxymethyl)-2,3,4,5,8,9-hexahydrooxonine-2-carbaldehyde
• CAS: 958461-32-0
• 化学式: C₂₄H₃₈O₄Si
• 分子量: 418.649
• InChiKey: ICKQAKBCTGBBPO-KPCLNVDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.68
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R,6Z,9R)-3-[tert-butyl(dimethyl)silyl]oxy-7-methyl-9-(phenylmethoxymethyl)-2,3,4,5,8,9-hexahydrooxonine-2-carbaldehyde 、 甲基三苯基溴化膦 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到tert-butyl-[[(2R,3R,6Z,9R)-2-ethenyl-7-methyl-9-(phenylmethoxymethyl)-2,3,4,5,8,9-hexahydrooxonin-3-yl]oxy]-dimethylsilane
  参考文献：
  名称：

  An Intramolecular Diels−Alder Strategy for the Asbestinins:  Enantioselective Total Syntheses of 11-Acetoxy-4-deoxyasbestinin D and Asbestinin-12

  摘要：

  [Graphics]The enantioselective total syntheses of 11-acetoxy-4-deoxyasbestinin D and asbestinin-12 have been completed. A glycolate aldol reaction provided a diene useful for ring-closing metathesis to form an oxonene, which was ultimately employed as a template to execute a highly stereoselective intramolecular Diels-Alder cycloaddition, forming the hydroisobenzofuran moiety. The absolute configuration of the asbestinin subclass was confirmed via these synthetic efforts.

  DOI：

  10.1021/jo0712695
• 作为产物：
  描述：

  [(2R,3R,6Z,9R)-3-[tert-butyl(dimethyl)silyl]oxy-7-methyl-9-(phenylmethoxymethyl)-2,3,4,5,8,9-hexahydrooxonin-2-yl]methanol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到(2S,3R,6Z,9R)-3-[tert-butyl(dimethyl)silyl]oxy-7-methyl-9-(phenylmethoxymethyl)-2,3,4,5,8,9-hexahydrooxonine-2-carbaldehyde
  参考文献：
  名称：

  An Intramolecular Diels−Alder Strategy for the Asbestinins:  Enantioselective Total Syntheses of 11-Acetoxy-4-deoxyasbestinin D and Asbestinin-12

  摘要：

  [Graphics]The enantioselective total syntheses of 11-acetoxy-4-deoxyasbestinin D and asbestinin-12 have been completed. A glycolate aldol reaction provided a diene useful for ring-closing metathesis to form an oxonene, which was ultimately employed as a template to execute a highly stereoselective intramolecular Diels-Alder cycloaddition, forming the hydroisobenzofuran moiety. The absolute configuration of the asbestinin subclass was confirmed via these synthetic efforts.

  DOI：

  10.1021/jo0712695

文献信息

• An Intramolecular Diels−Alder Strategy for the Asbestinins:  Enantioselective Total Syntheses of 11-Acetoxy-4-deoxyasbestinin D and Asbestinin-12
  作者：Michael T. Crimmins、J. Michael Ellis

  DOI：10.1021/jo0712695

  日期：2008.3.1

  [Graphics]The enantioselective total syntheses of 11-acetoxy-4-deoxyasbestinin D and asbestinin-12 have been completed. A glycolate aldol reaction provided a diene useful for ring-closing metathesis to form an oxonene, which was ultimately employed as a template to execute a highly stereoselective intramolecular Diels-Alder cycloaddition, forming the hydroisobenzofuran moiety. The absolute configuration of the asbestinin subclass was confirmed via these synthetic efforts.