(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]-7,15,17-trihydroxy-2,14-dimethoxy-4,6,8,10,16-pentamethylnonadeca-2,4,10,12-tetraenoic acid | 381247-02-5

• 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: (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]-7,15,17-trihydroxy-2,14-dimethoxy-4,6,8,10,16-pentamethylnonadeca-2,4,10,12-tetraenoic acid
• CAS: 381247-02-5
• 化学式: C₅₀H₉₄O₉S₂Si₂
• 分子量: 959.594
• InChiKey: MIVCQZZOTPAASK-JPDUWYQVSA-N

物化性质

• 沸点：
  884.2±65.0 °C(predicted)
• 密度：
  1.029±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.11
• 重原子数：
  63
• 可旋转键数：
  27
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  186
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (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]-7,15,17-trihydroxy-2,14-dimethoxy-4,6,8,10,16-pentamethylnonadeca-2,4,10,12-tetraenoic acid 在 4-二甲氨基吡啶 、 对甲苯磺酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 calcium carbonate 、 mercury dichloride 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 7.33h， 生成 巴佛洛霉素A1
  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：

  (3R,4S,5S)-4-Benzyloxymethoxy-7-methoxymethoxy-3,5-dimethyl-heptane-1,2-diol 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 palladium dihydroxide 、 水 吡啶 、 咪唑 、 manganese(IV) oxide 、 氢氧化钾 、 sodium periodate 、 二氯二茂锆 、 三苯胂 、 B-溴代邻苯二氧硼烷 、 四丁基氟化铵 、 氢气 、 二异丁基氢化铝 、 potassium carbonate 、 戴斯-马丁氧化剂 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 N,N-二异丙基乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 128.67h， 生成 (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]-7,15,17-trihydroxy-2,14-dimethoxy-4,6,8,10,16-pentamethylnonadeca-2,4,10,12-tetraenoic acid
  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.