tert-butyl-[(4R,5S,6R)-6-((S)-1-[1,3]dithian-2-yl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl-methoxy]-diphenylsilane | 381246-82-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl-[(4R,5S,6R)-6-((S)-1-[1,3]dithian-2-yl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl-methoxy]-diphenylsilane
• 英文别名: tert-butyl-[[(4R,5S,6R)-6-[(1S)-1-(1,3-dithian-2-yl)ethyl]-2,2,5-trimethyl-1,3-dioxan-4-yl]methoxy]-diphenylsilane
• CAS: 381246-82-8
• 化学式: C₃₀H₄₄O₃S₂Si
• 分子量: 544.895
• InChiKey: RQTNIMHBCNKUBB-GXVHRJHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.55
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  78.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl-[(4R,5S,6R)-6-((S)-1-[1,3]dithian-2-yl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl-methoxy]-diphenylsilane 在 六甲基磷酰三胺 、 pyridine-SO3 complex 、 四丁基氟化铵 、 叔丁基锂 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 正戊烷 为溶剂， 反应 15.0h， 生成 (1R)-1-[(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]dioxan-4-yl]-prop-2-yn-1-ol
  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：

  (2R,3R,4S,5R,6S)-2,6,7-Trihydroxy-4-methoxymethoxy-3,5-dimethyl-heptanoic acid methyl ester 在 咪唑 、 sodium tetrahydroborate 、 sodium periodate 、 三氟化硼乙醚 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 11.5h， 生成 tert-butyl-[(4R,5S,6R)-6-((S)-1-[1,3]dithian-2-yl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl-methoxy]-diphenylsilane
  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.