(3S)-3-O-tert-butyldimethylsilyl-6-O-trimethylsilyl-2-methyl-8-trimethylsilyl-6-(trimethylsilyl)ethynyl-(4E)-octen-7-yne-3,6-diol | 693782-92-2

• 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: (3S)-3-O-tert-butyldimethylsilyl-6-O-trimethylsilyl-2-methyl-8-trimethylsilyl-6-(trimethylsilyl)ethynyl-(4E)-octen-7-yne-3,6-diol
• 英文别名: tert-butyl-dimethyl-[(E,3S)-2-methyl-8-trimethylsilyl-6-(2-trimethylsilylethynyl)-6-trimethylsilyloxyoct-4-en-7-yn-3-yl]oxysilane
• CAS: 693782-92-2
• 化学式: C₂₆H₅₂O₂Si₄
• 分子量: 509.04
• InChiKey: BLOVQJCKNQUZCJ-IKPXGLPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.94
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  烯丙基三甲基硅烷 、 (3S)-3-O-tert-butyldimethylsilyl-6-O-trimethylsilyl-2-methyl-8-trimethylsilyl-6-(trimethylsilyl)ethynyl-(4E)-octen-7-yne-3,6-diol 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以78%的产率得到(4R)-4-[(1S)-1-(tert-butyldimethylsiloxy)-2-methyl]propyl-6-(trimethylsilyl)ethynyl-8-trimethylsilyl-1,5-octadien-7-yne
  参考文献：
  名称：

  Diastereoselective Allylations of Allyl−Propargyl Hybrid Cations:  Synthesis of Conjugated 1,5-Dien-7-yne Frameworks Bearing C(4)-Stereogenic Centers

  摘要：

  Chiral C(4)-substituted (E)- or (Z)-1-alkynyl-1-trimethylsilyloxy-2-butene systems provide anti-(Z) or syn-(Z) conjugated dienyne, with a very high level of stereocontrol, on treatment with (BF3OEt2)-O-. in CH2Cl2 at -50 degreesC in the presence of allyltrimethylsilane. The Cieplak conformation for (E)-substrates and neighboring-group participation for (2)-substrates are considered to be responsible for the stereochemical consequences.

  DOI：

  10.1021/ol049847g
• 作为产物：
  描述：

  (E)-(S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-hex-2-enoic acid ethyl ester 在 咪唑 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 (3S)-3-O-tert-butyldimethylsilyl-6-O-trimethylsilyl-2-methyl-8-trimethylsilyl-6-(trimethylsilyl)ethynyl-(4E)-octen-7-yne-3,6-diol
  参考文献：
  名称：

  Diastereoselective Allylations of Allyl−Propargyl Hybrid Cations:  Synthesis of Conjugated 1,5-Dien-7-yne Frameworks Bearing C(4)-Stereogenic Centers

  摘要：

  Chiral C(4)-substituted (E)- or (Z)-1-alkynyl-1-trimethylsilyloxy-2-butene systems provide anti-(Z) or syn-(Z) conjugated dienyne, with a very high level of stereocontrol, on treatment with (BF3OEt2)-O-. in CH2Cl2 at -50 degreesC in the presence of allyltrimethylsilane. The Cieplak conformation for (E)-substrates and neighboring-group participation for (2)-substrates are considered to be responsible for the stereochemical consequences.

  DOI：

  10.1021/ol049847g