| 381246-72-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• CAS: 381246-72-6
• 化学式: C₅₂H₁₁₀O₅S₂Si₃Sn
• 分子量: 1082.54
• InChiKey: YYYVMVLWQYKCFG-JJSTZRQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.0
• 重原子数：
  63
• 可旋转键数：
  33
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  、 (6R,7S,8S)-11-iodo-2-methoxy-4,6,8,10-tetramethyl-7-(triethylsilanyloxy)-undeca-2,4,10-trans-trienoic acid methyl ester 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 三苯胂 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 以60%的产率得到methyl (2Z,4E,6R,7S,8S,10E,12E,14S,15R,16S,17R,18S)-18-[2-[(2R,3S,4R)-2,4-bis[[tert-butyl(dimethyl)silyl]oxy]-3,5-dimethylhexyl]-1,3-dithian-2-yl]-17-hydroxy-2,14-dimethoxy-4,6,8,10,16-pentamethyl-7,15-bis(triethylsilyloxy)nonadeca-2,4,10,12-tetraenoate
  参考文献：
  名称：

  Total Synthesis of Bafilomycin A₁ Relying on Iterative 1,2-Induction in Acyclic Precursors

  摘要：

  The macrolide bafilomycin A(1) was synthesized starting from D-valine and D-mannitol as chiral progenitors of propionate units. Acyclic subunits corresponding to different parts of the molecule were constructed based on an iterative 1,2-asymmetric induction protocol as a distinctive feature of the synthesis. The assembly of two segments encompassing the entire carbon framework of the macrolide was achieved by using a Stille coupling. The resulting seco-ester was further manipulated to provide crystalline bafilomycin A(1) via a conventional carbodiimide-mediated Keck-type macrolactonization.

  DOI：

  10.1021/ja011452u
• 作为产物：
  描述：

  三正丁基氢锡 、 (2S,3R,4S,5R,6S)-2-{2-[(2R,3S,4R)-2,4-bis(tert-butyldimethylsilanyloxy)-3,5-dimethylhexyl]-[1,3]dithian-2-yl}-6-methoxy-4-methyl-5-triethylsilanyloxy-oct-7-yn-3-ol 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到
  参考文献：
  名称：

  Total Synthesis of Bafilomycin A₁ Relying on Iterative 1,2-Induction in Acyclic Precursors

  摘要：

  The macrolide bafilomycin A(1) was synthesized starting from D-valine and D-mannitol as chiral progenitors of propionate units. Acyclic subunits corresponding to different parts of the molecule were constructed based on an iterative 1,2-asymmetric induction protocol as a distinctive feature of the synthesis. The assembly of two segments encompassing the entire carbon framework of the macrolide was achieved by using a Stille coupling. The resulting seco-ester was further manipulated to provide crystalline bafilomycin A(1) via a conventional carbodiimide-mediated Keck-type macrolactonization.

  DOI：

  10.1021/ja011452u

文献信息

• Total Synthesis of Bafilomycin A₁ Relying on Iterative 1,2-Induction in Acyclic Precursors
  作者：Stephen Hanessian、Jianguo Ma、Wengui Wang

  DOI：10.1021/ja011452u

  日期：2001.10.1

  The macrolide bafilomycin A(1) was synthesized starting from D-valine and D-mannitol as chiral progenitors of propionate units. Acyclic subunits corresponding to different parts of the molecule were constructed based on an iterative 1,2-asymmetric induction protocol as a distinctive feature of the synthesis. The assembly of two segments encompassing the entire carbon framework of the macrolide was achieved by using a Stille coupling. The resulting seco-ester was further manipulated to provide crystalline bafilomycin A(1) via a conventional carbodiimide-mediated Keck-type macrolactonization.