(R)-4-benzyl-3-[(Z)-(2R,3S,4R,5S,6S)-3-(tert-butyldimethylsilanyloxy)-2,4,6-trimethyl-5-triethylsilanyloxydeca-7,9-dienoyl]-oxazolidin-2-one | 649755-90-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (R)-4-benzyl-3-[(Z)-(2R,3S,4R,5S,6S)-3-(tert-butyldimethylsilanyloxy)-2,4,6-trimethyl-5-triethylsilanyloxydeca-7,9-dienoyl]-oxazolidin-2-one
• 英文别名: (4R)-4-benzyl-3-[(2R,3S,4R,5S,6S,7Z)-3-[tert-butyl(dimethyl)silyl]oxy-2,4,6-trimethyl-5-triethylsilyloxydeca-7,9-dienoyl]-1,3-oxazolidin-2-one
• CAS: 649755-90-8
• 化学式: C₃₅H₅₉NO₅Si₂
• 分子量: 630.028
• InChiKey: JFDGBPDGMIWBRQ-QYNSCGHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.01
• 重原子数：
  43.0
• 可旋转键数：
  16.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-4-benzyl-3-[(Z)-(2R,3S,4R,5S,6S)-3-(tert-butyldimethylsilanyloxy)-2,4,6-trimethyl-5-triethylsilanyloxydeca-7,9-dienoyl]-oxazolidin-2-one 在 锂硼氢 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 1.5h， 生成 (3Z,5S,6S,7R,8R,9S)-8-(tert-butyldimethylsilyloxy)-10-hydroxy-6-(triethylsilyloxy)-5,7,9-trimethyldeca-1,3-diene
  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：

  (3R,4S,5S)-3,5-dimethyl-4-[(triethylsilanyl)oxy]tetrahydropyran-2-one 在 2,6-二甲基吡啶 、 chromium dichloride 、 三氟甲磺酸二丁硼 、 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 11.17h， 生成 (R)-4-benzyl-3-[(Z)-(2R,3S,4R,5S,6S)-3-(tert-butyldimethylsilanyloxy)-2,4,6-trimethyl-5-triethylsilanyloxydeca-7,9-dienoyl]-oxazolidin-2-one
  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

文献信息

• [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.