(4R,5S,6R)-6-((S)-1-{2-[(2R,3S,4R)-2,4-bis(tert-butyldimethylsilanyloxy)-3,5-dimethylhexyl]-[1,3]dithian-2-yl}-ethyl)-2,2,5-trimethyl-[1,3]dioxane-4-carbaldehyde | 381246-84-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: (4R,5S,6R)-6-((S)-1-{2-[(2R,3S,4R)-2,4-bis(tert-butyldimethylsilanyloxy)-3,5-dimethylhexyl]-[1,3]dithian-2-yl}-ethyl)-2,2,5-trimethyl-[1,3]dioxane-4-carbaldehyde
• 英文别名: (4R,5S,6R)-6-[(1S)-1-[2-[(2R,3S,4R)-2,4-bis[[tert-butyl(dimethyl)silyl]oxy]-3,5-dimethylhexyl]-1,3-dithian-2-yl]ethyl]-2,2,5-trimethyl-1,3-dioxane-4-carbaldehyde
• CAS: 381246-84-0
• 化学式: C₃₄H₆₈O₅S₂Si₂
• 分子量: 677.214
• InChiKey: BJVMTTFSQFWWAM-WYDRRVITSA-N

物化性质

• 沸点：
  629.2±55.0 °C(predicted)
• 密度：
  0.987±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.01
• 重原子数：
  43
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4R,5S,6R)-6-((S)-1-{2-[(2R,3S,4R)-2,4-bis(tert-butyldimethylsilanyloxy)-3,5-dimethylhexyl]-[1,3]dithian-2-yl}-ethyl)-2,2,5-trimethyl-[1,3]dioxane-4-carbaldehyde 在 camphor-10-sulfonic acid 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.5h， 生成
  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：

  D-缬氨酸 在 palladium dihydroxide 咪唑 、 2,6-二甲基吡啶 、 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 三甲基氯硅烷 、 草酰氯 、 pyridine-SO3 complex 、 硫酸 、 四丁基氟化铵 、 氢气 、 碘 、 叔丁基锂 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 甲苯 、 正戊烷 为溶剂， -78.0~130.0 ℃ 、101.33 kPa 条件下， 反应 113.5h， 生成 (4R,5S,6R)-6-((S)-1-{2-[(2R,3S,4R)-2,4-bis(tert-butyldimethylsilanyloxy)-3,5-dimethylhexyl]-[1,3]dithian-2-yl}-ethyl)-2,2,5-trimethyl-[1,3]dioxane-4-carbaldehyde
  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.