1-[(3aS,4S,5S,7aR)-5-(tert-Butyl-diphenyl-silanyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl]-ethanone | 864948-17-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[(3aS,4S,5S,7aR)-5-(tert-Butyl-diphenyl-silanyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl]-ethanone
• 英文别名: 1-[(3aS,4S,5S,7aR)-5-[tert-butyl(diphenyl)silyl]oxy-2,2-dimethyl-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxol-4-yl]ethanone
• CAS: 864948-17-4
• 化学式: C₂₇H₃₆O₄Si
• 分子量: 452.666
• InChiKey: ALTPZYQJSINSDG-ZYQDXHPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  2-(4-Methyl-pent-3-ene-1-sulfonyl)-benzothiazole 、 1-[(3aS,4S,5S,7aR)-5-(tert-Butyl-diphenyl-silanyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl]-ethanone 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 tert-Butyl-[(3aS,4S,5S,7aR)-4-((Z)-1,5-dimethyl-hexa-1,4-dienyl)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yloxy]-diphenyl-silane 、 tert-Butyl-[(3aS,4S,5S,7aR)-4-((E)-1,5-dimethyl-hexa-1,4-dienyl)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yloxy]-diphenyl-silane
  参考文献：
  名称：

  Oxocarbenium Ion Cyclizations for C-Branched Cyclitols:  Synthesis of a Relay Intermediate for Fumagillin Analogues

  摘要：

  [GRAPHICS]A highly stereoselective oxocarbenium ion-alkene cyclization for synthesis of C-branched cylitols is described. This methodology was applied to 10S, a potentially versatile intermediate for side-chain analogues of the antiangiogenic agent fumagillin. Compound 105 was subsequently converted to diene 5. Because racemic 5 has been converted to racemic fumagillin, this synthesis of 5 constitutes a formal synthesis of the natural product.

  DOI：

  10.1021/jo050888f
• 作为产物：
  描述：

  tert-Butyl-((3aS,4S,5S,7aR)-4-isopropenyl-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yloxy)-diphenyl-silane 在 氧气 、 臭氧 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 以85%的产率得到1-[(3aS,4S,5S,7aR)-5-(tert-Butyl-diphenyl-silanyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl]-ethanone
  参考文献：
  名称：

  Oxocarbenium Ion Cyclizations for C-Branched Cyclitols:  Synthesis of a Relay Intermediate for Fumagillin Analogues

  摘要：

  [GRAPHICS]A highly stereoselective oxocarbenium ion-alkene cyclization for synthesis of C-branched cylitols is described. This methodology was applied to 10S, a potentially versatile intermediate for side-chain analogues of the antiangiogenic agent fumagillin. Compound 105 was subsequently converted to diene 5. Because racemic 5 has been converted to racemic fumagillin, this synthesis of 5 constitutes a formal synthesis of the natural product.

  DOI：

  10.1021/jo050888f

文献信息

• Oxocarbenium Ion Cyclizations for C-Branched Cyclitols:  Synthesis of a Relay Intermediate for Fumagillin Analogues
  作者：Fatoumata Camara、Johana Angarita、David R. Mootoo

  DOI：10.1021/jo050888f

  日期：2005.8.1

  [GRAPHICS]A highly stereoselective oxocarbenium ion-alkene cyclization for synthesis of C-branched cylitols is described. This methodology was applied to 10S, a potentially versatile intermediate for side-chain analogues of the antiangiogenic agent fumagillin. Compound 105 was subsequently converted to diene 5. Because racemic 5 has been converted to racemic fumagillin, this synthesis of 5 constitutes a formal synthesis of the natural product.