(3R,4S,5S)-3,5-dimethyl-4-[(triethylsilanyl)oxy]tetrahydropyran-2-one | 649755-77-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3R,4S,5S)-3,5-dimethyl-4-[(triethylsilanyl)oxy]tetrahydropyran-2-one
• 英文别名: (3R,4S,5S)-3,5-dimethyl-4-triethylsilyloxyoxan-2-one
• CAS: 649755-77-1
• 化学式: C₁₃H₂₆O₃Si
• 分子量: 258.433
• InChiKey: PTLNECZSIFIOOE-TUAOUCFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S)-3,5-dimethyl-4-[(triethylsilanyl)oxy]tetrahydropyran-2-one 在 chromium dichloride 、 三氧化硫吡啶 、 potassium hydride 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 甲苯 、 mineral oil 为溶剂， 反应 6.42h， 生成 (Z)-(2R,3S,4S)-2,4-dimethyl-3-triethylsilanyloxyocta-5,7-dienal
  参考文献：
  名称：

  A Formal Synthesis of (+)-Discodermolide

  摘要：

  Herein, we report the formal synthesis of (+)-discodermolide (1), a promising anticancer agent of sponge origin, in 24 linear steps, with 35 steps in total. The route proceeds from lactone 2, a building block containing the common 1,2-anti-2,3-syn stereotriad found in each of the three subunits, methyl ketone 4 (C-1-C-6), vinyl iodide 7 (C-9--C-14), and iodide 8 (C-15-C-24) utilized for the construction of L The key fragment union was achieved by a Suzuki cross-coupling between 7 and 8.

  DOI：

  10.1021/op049807s
• 作为产物：
  描述：

  (R)-3-[(2R,3S,4S)-5-hydroxy-2,4-dimethyl-3-(triethylsilanyloxy)pentanoyl]-4-isopropyl-5,5-diphenyloxazolidin-2-one 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以69%的产率得到(3R,4S,5S)-3,5-dimethyl-4-[(triethylsilanyl)oxy]tetrahydropyran-2-one
  参考文献：
  名称：

  [EN] SYNTHESIS OF DISCODERMOLIDE
  [FR] SYNTHESE DU DISCODERMOLIDE

  摘要：

  该发明涉及一种制备discodermolide的过程，用于制备制造discodermolide和discodermolide类似物的中间体，以及在过程中获得的中间体。其中，该过程通过式（IV）的四烯体进行。

  公开号：

  WO2004009574A1

文献信息

• A Practical Building Block for the Synthesis of Discodermolide
  作者：Olivier Loiseleur、Guido Koch、Trixie Wagner

  DOI：10.1021/op049950l

  日期：2004.7.1

  A new highly diastereoselective and practical route to the lactone 6a which is used as a key building block for the total synthesis of the microtubule-stabilizing anticancer agent discodermolide is reported. This exploits the chiral auxiliary (4R)4-isopropyl-5,5-diphenyloxazolidin-2-one (7) which conveys crystallinity to the synthetic intermediates throughout the entire process. Purifications can thus be performed by recrystallization, avoiding chromatography to afford the final product in high enantiomeric purity. The overall efficiency is augmented by the facile recovery of the auxiliary by precipitation at the end of the sequence.
• [EN] SYNTHESIS OF DISCODERMOLIDE<br/>[FR] SYNTHESE DU DISCODERMOLIDE
  申请人：NOVARTIS AG

  公开号：WO2004009574A1

  公开（公告）日：2004-01-29

  The invention relates to a process for preparing discodermolide, for preparing intermediates for the manufacture of discodermolide and discodermolide analogues and to the intermediates obtained during the process. Wherein the process proceeds via a tetraene of formula (IV).

  该发明涉及一种制备discodermolide的过程，用于制备制造discodermolide和discodermolide类似物的中间体，以及在过程中获得的中间体。其中，该过程通过式（IV）的四烯体进行。
• A Formal Synthesis of (+)-Discodermolide
  作者：Olivier Loiseleur、Guido Koch、Jacques Cercus、Friedrich Schürch

  DOI：10.1021/op049807s

  日期：2005.5.1

  Herein, we report the formal synthesis of (+)-discodermolide (1), a promising anticancer agent of sponge origin, in 24 linear steps, with 35 steps in total. The route proceeds from lactone 2, a building block containing the common 1,2-anti-2,3-syn stereotriad found in each of the three subunits, methyl ketone 4 (C-1-C-6), vinyl iodide 7 (C-9--C-14), and iodide 8 (C-15-C-24) utilized for the construction of L The key fragment union was achieved by a Suzuki cross-coupling between 7 and 8.