tert-Butyl-((3aS,4S,5S,7aR)-4-isopropenyl-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yloxy)-diphenyl-silane | 864948-15-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-Butyl-((3aS,4S,5S,7aR)-4-isopropenyl-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yloxy)-diphenyl-silane
• 英文别名: [(3aS,4S,5S,7aR)-2,2-dimethyl-4-prop-1-en-2-yl-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxol-5-yl]oxy-tert-butyl-diphenylsilane
• CAS: 864948-15-2
• 化学式: C₂₈H₃₈O₃Si
• 分子量: 450.693
• InChiKey: TYMDMLGWWRURQT-BKKFENPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.44
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 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-{1-[2-((4R,5R)-2,2-dimethyl-5-phenylsulfanyl-[1,3]dioxolan-4-yl)-ethyl]-3-methyl-but-2-enyloxy}-diphenyl-silane 在 2,6-二叔丁基-4-甲基吡啶 、 4 A molecular sieve 、 三氟甲烷磺酸甲酯 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以74%的产率得到tert-Butyl-((3aS,4S,5S,7aR)-4-isopropenyl-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

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.