methyl (E)-6-((tert-butyldiphenylsilyl)oxy)-3-(tributylstannyl)hex-2-enoate | 1229041-69-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (E)-6-((tert-butyldiphenylsilyl)oxy)-3-(tributylstannyl)hex-2-enoate
• CAS: 1229041-69-3
• 化学式: C₃₅H₅₆O₃SiSn
• 分子量: 671.623
• InChiKey: WPVZTUIYUPWTOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.83
• 重原子数：
  40.0
• 可旋转键数：
  18.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl (E)-6-((tert-butyldiphenylsilyl)oxy)-3-(tributylstannyl)hex-2-enoate 在 2,6-二甲基吡啶 、 silver hexafluoroantimonate 、 2,6-二叔丁基-4-甲基吡啶 、 草酰氯 、 tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) 、 三苯基膦氯金 、 偶氮二甲酸二异丙酯 、 dimethyl(metylthio)sulfonium triflate 、 四丁基氟化铵 、 碘 、 仲丁基锂 、 二异丁基氢化铝 、 potassium carbonate 、 臭氧 、 二甲基亚砜 、 苯硫酚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 异丙醇 、 乙腈 、 苯 为溶剂， 反应 12.75h， 生成
  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：

  三正丁基氢锡 、 Methyl 6-(tert-butyldiphenylsiloxy)-2-hexynoate 在 copper(I) bromide dimethylsulfide complex 、 lithium diisopropyl amide 作用下， 以93%的产率得到methyl (E)-6-((tert-butyldiphenylsilyl)oxy)-3-(tributylstannyl)hex-2-enoate
  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