(2R,3R)-3-but-3-enyl-3-[[tert-butyl(diphenyl)silyl]oxymethyl]oxirane-2-carbaldehyde | 916433-73-3

• 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: (2R,3R)-3-but-3-enyl-3-[[tert-butyl(diphenyl)silyl]oxymethyl]oxirane-2-carbaldehyde
• CAS: 916433-73-3
• 化学式: C₂₄H₃₀O₃Si
• 分子量: 394.586
• InChiKey: JGOGRZYLSRZZEN-LADGPHEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-but-3-enyl-3-[[tert-butyl(diphenyl)silyl]oxymethyl]oxirane-2-carbaldehyde 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 Petroleum ether 为溶剂， 反应 3.58h， 生成 (3-but-3-enyl-3-hydroxymethyl-oxiranyl)-[3,6-dimethoxy-2-(2-methyl-allyl)-phenyl]-methanol
  参考文献：
  名称：

  Highly Convergent Three Component Benzyne Coupling:  The Total Synthesis of ent-Clavilactone B

  摘要：

  The first total synthesis of (+)-clavilactone B, a potent antifungal agent and novel tyrosine kinase inhibitor, is described. The absolute configuration of clavilactones has been unambiguously established by using Sharpless asymmetric epoxidation to generate the enantiomerically pure substrate. The strategy highlights the use of a powerful and convergent three-component benzyne coupling with a methylallyl Grignard and a chiral epoxy-aldehyde to generate two C-C bonds and install the carbon skeleton of clavilactone. Oxidative lactonization, ten-membered ring construction by ring closing metathesis, and oxidation gave clavilactone B.

  DOI：

  10.1021/ja0662671
• 作为产物：
  描述：

  tert-butyl(diphenyl)(2-propynyloxy)silane 在 L-(+)-酒石酸二乙酯 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 正丁基锂 、 草酰氯 、 4 A molecular sieve 、 碘 、 二异丁基氢化铝 、 magnesium 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 癸烷 、 正己烷 、 二氯甲烷 、 甲苯 、 Petroleum ether 为溶剂， 反应 57.09h， 生成 (2R,3R)-3-but-3-enyl-3-[[tert-butyl(diphenyl)silyl]oxymethyl]oxirane-2-carbaldehyde
  参考文献：
  名称：

  Highly Convergent Three Component Benzyne Coupling:  The Total Synthesis of ent-Clavilactone B

  摘要：

  The first total synthesis of (+)-clavilactone B, a potent antifungal agent and novel tyrosine kinase inhibitor, is described. The absolute configuration of clavilactones has been unambiguously established by using Sharpless asymmetric epoxidation to generate the enantiomerically pure substrate. The strategy highlights the use of a powerful and convergent three-component benzyne coupling with a methylallyl Grignard and a chiral epoxy-aldehyde to generate two C-C bonds and install the carbon skeleton of clavilactone. Oxidative lactonization, ten-membered ring construction by ring closing metathesis, and oxidation gave clavilactone B.

  DOI：

  10.1021/ja0662671

文献信息

• Highly Convergent Three Component Benzyne Coupling:  The Total Synthesis of <i>ent</i>-Clavilactone B
  作者：Igor Larrosa、Marianne I. Da Silva、Patricio M. Gómez、Peter Hannen、Eunjung Ko、Steven R. Lenger、Simon R. Linke、Andrew J. P. White、Donna Wilton、Anthony G. M. Barrett

  DOI：10.1021/ja0662671

  日期：2006.11.1

  The first total synthesis of (+)-clavilactone B, a potent antifungal agent and novel tyrosine kinase inhibitor, is described. The absolute configuration of clavilactones has been unambiguously established by using Sharpless asymmetric epoxidation to generate the enantiomerically pure substrate. The strategy highlights the use of a powerful and convergent three-component benzyne coupling with a methylallyl Grignard and a chiral epoxy-aldehyde to generate two C-C bonds and install the carbon skeleton of clavilactone. Oxidative lactonization, ten-membered ring construction by ring closing metathesis, and oxidation gave clavilactone B.