(E)-(3S,6R)-6-(tert-Butyl-diphenyl-silanyloxy)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-4-enoic acid dimethylamide | 162680-08-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-(3S,6R)-6-(tert-Butyl-diphenyl-silanyloxy)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-4-enoic acid dimethylamide
• 英文别名: (E,3S,6R)-6-[tert-butyl(diphenyl)silyl]oxy-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-N,N-dimethylhept-4-enamide
• CAS: 162680-08-2
• 化学式: C₃₀H₄₃NO₄Si
• 分子量: 509.761
• InChiKey: UNFGIRYKWMJNRB-OSLCTNOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-(3S,6R)-6-(tert-Butyl-diphenyl-silanyloxy)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-4-enoic acid dimethylamide 在 溶剂黄146 作用下， 反应 48.0h， 以79%的产率得到(4S,5S)-4-[(E)-(R)-3-(tert-Butyl-diphenyl-silanyloxy)-but-1-enyl]-5-hydroxymethyl-dihydro-furan-2-one
  参考文献：
  名称：

  A 1,2-O-O-Silyl-Migration-Claisen-Rearrangement-Sn2'-Displacement Sequence in the Stereoselective Synthesis of 5-Oxaprostanoid Derivatives

  摘要：

  A novel stereocontrolled route to 5-oxaprostaglandin and PGF intermediates is described, which starts from the ene-diols (6/7) and uses a sequence of Claisen rearrangement, 1,2-O-O-silyl migration and S(N)2'-cyclization reactions (9b --> 10a/b via 11a/b).

  DOI：

  10.3987/com-94-s15
• 作为产物：
  描述：

  dimethyl (3R)-3-((tert-butyl(diphenyl)silyl)oxy)-2-oxobutylphosphonate 在 L-Selectride 、 lithium diisopropyl amide 作用下， 反应 24.0h， 生成 (E)-(3S,6R)-6-(tert-Butyl-diphenyl-silanyloxy)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-4-enoic acid dimethylamide
  参考文献：
  名称：

  A 1,2-O-O-Silyl-Migration-Claisen-Rearrangement-Sn2'-Displacement Sequence in the Stereoselective Synthesis of 5-Oxaprostanoid Derivatives

  摘要：

  A novel stereocontrolled route to 5-oxaprostaglandin and PGF intermediates is described, which starts from the ene-diols (6/7) and uses a sequence of Claisen rearrangement, 1,2-O-O-silyl migration and S(N)2'-cyclization reactions (9b --> 10a/b via 11a/b).

  DOI：

  10.3987/com-94-s15

文献信息

• A 1,2-O-O-Silyl-Migration-Claisen-Rearrangement-Sn2'-Displacement Sequence in the Stereoselective Synthesis of 5-Oxaprostanoid Derivatives
  作者：Johann Mulzer、Stefan Greifenberg

  DOI：10.3987/com-94-s15

  日期：——

  A novel stereocontrolled route to 5-oxaprostaglandin and PGF intermediates is described, which starts from the ene-diols (6/7) and uses a sequence of Claisen rearrangement, 1,2-O-O-silyl migration and S(N)2'-cyclization reactions (9b --> 10a/b via 11a/b).