(E)-6-((tert-butyldiphenylsilyl)oxy)-3-(tributylstannyl)hex-2-en-1-ol | 1229041-70-6

• 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: (E)-6-((tert-butyldiphenylsilyl)oxy)-3-(tributylstannyl)hex-2-en-1-ol
• CAS: 1229041-70-6
• 化学式: C₃₄H₅₆O₂SiSn
• 分子量: 643.613
• InChiKey: XQGXBIKAESJRDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.65
• 重原子数：
  38.0
• 可旋转键数：
  18.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-6-((tert-butyldiphenylsilyl)oxy)-3-(tributylstannyl)hex-2-en-1-ol 在 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 碘 、 仲丁基锂 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.75h， 生成 tert-butyl((E)-4-((1SR,2SR,4RS)-2-(2,2-dimethoxyethyl)-4-methyl-1-(trimethylsilyloxy)cyclopentyl)-6-phenoxyhex-4-enyloxy)diphenylsilane
  参考文献：
  名称：

  Total Synthesis of (+)-Sieboldine A: Evolution of a Pinacol-Terminated Cyclization Strategy

  摘要：

  This article describes synthetic studies that culminated in the first total synthesis of the Lycopodium alkaloid sieboldine A. During this study, a number of pinacol-terminated cationic cyclizations were examined to form the cis-hydrindanone core of sieboldine A. Of these, a mild Au(I)-promoted 1,6-enyne cyclization that was terminated by a semipinacol rearrangement proved to be most efficient. Fashioning the unprecedented N-hydroxyazacyclononane ring embedded within the bicyclo[5.2.1]decane-N,O-acetal moiety of sieboldine A was a formidable challenge. Ultimately, the enantioselective total synthesis of (+)-sieboldine A was completed by forming this ring in good yield by cyclization of a protected-hydroxylamine thioglycoside precursor.

  DOI：

  10.1021/jo300872y
• 作为产物：
  描述：

  Methyl 6-(tert-butyldiphenylsiloxy)-2-hexynoate 在 copper(I) bromide dimethylsulfide complex 、 二异丁基氢化铝 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-6-((tert-butyldiphenylsilyl)oxy)-3-(tributylstannyl)hex-2-en-1-ol
  参考文献：
  名称：

  Total Synthesis of (+)-Sieboldine A: Evolution of a Pinacol-Terminated Cyclization Strategy

  摘要：

  This article describes synthetic studies that culminated in the first total synthesis of the Lycopodium alkaloid sieboldine A. During this study, a number of pinacol-terminated cationic cyclizations were examined to form the cis-hydrindanone core of sieboldine A. Of these, a mild Au(I)-promoted 1,6-enyne cyclization that was terminated by a semipinacol rearrangement proved to be most efficient. Fashioning the unprecedented N-hydroxyazacyclononane ring embedded within the bicyclo[5.2.1]decane-N,O-acetal moiety of sieboldine A was a formidable challenge. Ultimately, the enantioselective total synthesis of (+)-sieboldine A was completed by forming this ring in good yield by cyclization of a protected-hydroxylamine thioglycoside precursor.

  DOI：

  10.1021/jo300872y