(3R,4S,5S,6S,7S,8E,11R,12S,13S,14R)-4-hydroxy-3,5,7,9,11,13,14-heptamethyl-6,12-bis(triethylsilyloxy)-1-oxacyclotetradec-8-ene-2,10-dione | 959151-22-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (3R,4S,5S,6S,7S,8E,11R,12S,13S,14R)-4-hydroxy-3,5,7,9,11,13,14-heptamethyl-6,12-bis(triethylsilyloxy)-1-oxacyclotetradec-8-ene-2,10-dione
• CAS: 959151-22-5
• 化学式: C₃₂H₆₂O₆Si₂
• 分子量: 599.012
• InChiKey: CMKZWXRRAAPDEE-QSDMIDDMSA-N

物化性质

• 沸点：
  618.3±55.0 °C(predicted)
• 密度：
  0.98±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.77
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S,6S,7S,8E,11R,12S,13S,14R)-4-hydroxy-3,5,7,9,11,13,14-heptamethyl-6,12-bis(triethylsilyloxy)-1-oxacyclotetradec-8-ene-2,10-dione 、 苯甲酰氯 在 吡啶 作用下， 反应 24.0h， 以96%的产率得到
  参考文献：
  名称：

  Deconstruction−Reconstruction Strategy for Accessing Valuable Polyketides. Preparation of the C15−C24 Stereopentad of Discodermolide

  摘要：

  An advanced, known intermediate for discodermolide synthesis was prepared by an efficient sequence from the readily available fermentation product oleandomycin. The scheme makes use of a new method for the direct cleavage of aminoglycosides, a critical double-bond isomerization, and a selective protection of two of three hydroxyl groups in a modified oleandolide. This synthesis illustrates a new strategy, "deconstruction-reconstruction", for accessing stereochemically complex polyketide building blocks.

  DOI：

  10.1021/ol702144u
• 作为产物：
  描述：

  (3R,4S,5R,6S,7S,8E,11R,12S,13R,14R)-4,6,12-trihydroxy-3,5,7,9,11,13,14-heptamethyl-1-oxacyclotetradec-8-ene-2,10-dione 、 三乙基硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以72%的产率得到(3R,4S,5S,6S,7S,8E,11R,12S,13S,14R)-4-hydroxy-3,5,7,9,11,13,14-heptamethyl-6,12-bis(triethylsilyloxy)-1-oxacyclotetradec-8-ene-2,10-dione
  参考文献：
  名称：

  Deconstruction−Reconstruction Strategy for Accessing Valuable Polyketides. Preparation of the C15−C24 Stereopentad of Discodermolide

  摘要：

  An advanced, known intermediate for discodermolide synthesis was prepared by an efficient sequence from the readily available fermentation product oleandomycin. The scheme makes use of a new method for the direct cleavage of aminoglycosides, a critical double-bond isomerization, and a selective protection of two of three hydroxyl groups in a modified oleandolide. This synthesis illustrates a new strategy, "deconstruction-reconstruction", for accessing stereochemically complex polyketide building blocks.

  DOI：

  10.1021/ol702144u

文献信息

• Deconstruction−Reconstruction Strategy for Accessing Valuable Polyketides. Preparation of the C15−C24 Stereopentad of Discodermolide
  作者：Kathlyn A. Parker、Peng Wang

  DOI：10.1021/ol702144u

  日期：2007.11.1

  An advanced, known intermediate for discodermolide synthesis was prepared by an efficient sequence from the readily available fermentation product oleandomycin. The scheme makes use of a new method for the direct cleavage of aminoglycosides, a critical double-bond isomerization, and a selective protection of two of three hydroxyl groups in a modified oleandolide. This synthesis illustrates a new strategy, "deconstruction-reconstruction", for accessing stereochemically complex polyketide building blocks.