ethyl (6S,7S,7aS)-7-(2,2-dimethylpropanoyloxy)-6-[dimethyl(prop-2-enyl)silyl]oxy-5-methylidene-3,6,7,7a-tetrahydro-2H-cyclopenta[b]pyridine-1-carboxylate | 905269-05-8

• 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: ethyl (6S,7S,7aS)-7-(2,2-dimethylpropanoyloxy)-6-[dimethyl(prop-2-enyl)silyl]oxy-5-methylidene-3,6,7,7a-tetrahydro-2H-cyclopenta[b]pyridine-1-carboxylate
• CAS: 905269-05-8
• 化学式: C₂₂H₃₅NO₅Si
• 分子量: 421.609
• InChiKey: HQEVFSUTJXNKGP-FHWLQOOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (6S,7S,7aS)-7-(2,2-dimethylpropanoyloxy)-6-[dimethyl(prop-2-enyl)silyl]oxy-5-methylidene-3,6,7,7a-tetrahydro-2H-cyclopenta[b]pyridine-1-carboxylate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) potassium fluoride 、 sodium methylate 、 potassium hydrogencarbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 (+)-streptazolin
  参考文献：
  名称：

  Stereoselective Total Synthesis of (+)-Streptazolin by Using a Temporary Silicon-Tethered RCM Strategy

  摘要：

  [GRAPHICS]A stereoselective total synthesis of (+)-streptazolin 1 was accomplished starting from readily available aminocyclopentenol (-)-7. The synthetic sequence highlights an intramolecular aldol condensation strategy to construct the piperidine core and a silicon-tethered ring-closing metathesis strategy to install the Z exocyclic ethylidene side chain of streptazolin. Separate protodesilylation and Tamao oxidation of a common intermediate 32 afforded streptazolin and the precursor for 13-hydroxystreptazolin. The overall yield for (+)-streptazolin 1 from aminocyclopentenol (-)-7 was 4.8% for a total of 16 steps.

  DOI：

  10.1021/jo060555y
• 作为产物：
  描述：

  ethyl (1S,2S,4R)-5-methylidene-3-oxa-10-azatricyclo[4.4.0.02,4]dec-6-ene-10-carboxylate 在 甲醇 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 potassium carbonate 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 ethyl (6S,7S,7aS)-7-(2,2-dimethylpropanoyloxy)-6-[dimethyl(prop-2-enyl)silyl]oxy-5-methylidene-3,6,7,7a-tetrahydro-2H-cyclopenta[b]pyridine-1-carboxylate
  参考文献：
  名称：

  Stereoselective Total Synthesis of (+)-Streptazolin by Using a Temporary Silicon-Tethered RCM Strategy

  摘要：

  [GRAPHICS]A stereoselective total synthesis of (+)-streptazolin 1 was accomplished starting from readily available aminocyclopentenol (-)-7. The synthetic sequence highlights an intramolecular aldol condensation strategy to construct the piperidine core and a silicon-tethered ring-closing metathesis strategy to install the Z exocyclic ethylidene side chain of streptazolin. Separate protodesilylation and Tamao oxidation of a common intermediate 32 afforded streptazolin and the precursor for 13-hydroxystreptazolin. The overall yield for (+)-streptazolin 1 from aminocyclopentenol (-)-7 was 4.8% for a total of 16 steps.

  DOI：

  10.1021/jo060555y

文献信息

• Stereoselective Total Synthesis of (+)-Streptazolin by Using a Temporary Silicon-Tethered RCM Strategy
  作者：Fangzheng Li、Marvin J. Miller

  DOI：10.1021/jo060555y

  日期：2006.7.1

  [GRAPHICS]A stereoselective total synthesis of (+)-streptazolin 1 was accomplished starting from readily available aminocyclopentenol (-)-7. The synthetic sequence highlights an intramolecular aldol condensation strategy to construct the piperidine core and a silicon-tethered ring-closing metathesis strategy to install the Z exocyclic ethylidene side chain of streptazolin. Separate protodesilylation and Tamao oxidation of a common intermediate 32 afforded streptazolin and the precursor for 13-hydroxystreptazolin. The overall yield for (+)-streptazolin 1 from aminocyclopentenol (-)-7 was 4.8% for a total of 16 steps.