(4S,5S)-5-But-3-enyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-hex-1-ene | 237736-78-6

• 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: (4S,5S)-5-But-3-enyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-hex-1-ene
• 英文别名: [(2S,3S)-2-but-3-enoxy-3-[tert-butyl(dimethyl)silyl]oxyhex-5-enoxy]-tert-butyl-dimethylsilane
• CAS: 237736-78-6
• 化学式: C₂₂H₄₆O₃Si₂
• 分子量: 414.776
• InChiKey: IYBMKFVOPLYHKZ-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.94
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  (4S,5S)-5-But-3-enyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-hex-1-ene 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以90%的产率得到(Z)-(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,4,7,8-tetrahydro-2H-oxocine
  参考文献：
  名称：

  Eight membered ethers via diene metathesis: Synthetic approach to laureatin natural products

  摘要：

  Ruthenium-mediated diene metathesis is applied to the synthesis of a range of oxocenes. The methodology is then utilised for the preparation of prelaureatin analogues. A successful synthesis of the 8-desalkyl analogue of prelaureatin in enantiomerically enriched form is described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00703-0
• 作为产物：
  描述：

  叔丁基二甲硅基三氟甲磺酸酯 、 烯丙基三丁基锡 、 (S)-2-But-3-enyloxy-3-(tert-butyl-dimethyl-silanyloxy)-propionaldehyde 在 magnesium bromide 作用下， 生成 (4S,5S)-5-But-3-enyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-hex-1-ene
  参考文献：
  名称：

  Eight membered ethers via diene metathesis: Synthetic approach to laureatin natural products

  摘要：

  Ruthenium-mediated diene metathesis is applied to the synthesis of a range of oxocenes. The methodology is then utilised for the preparation of prelaureatin analogues. A successful synthesis of the 8-desalkyl analogue of prelaureatin in enantiomerically enriched form is described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00703-0

文献信息

• Eight membered ethers via diene metathesis: Synthetic approach to laureatin natural products
  作者：Simon D. Edwards、Terence Lewis、Richard J.K. Taylor

  DOI：10.1016/s0040-4039(99)00703-0

  日期：1999.5

  Ruthenium-mediated diene metathesis is applied to the synthesis of a range of oxocenes. The methodology is then utilised for the preparation of prelaureatin analogues. A successful synthesis of the 8-desalkyl analogue of prelaureatin in enantiomerically enriched form is described. (C) 1999 Elsevier Science Ltd. All rights reserved.