(4S,5R)-5-(tert-butyldimethylsilyloxy)-7-(4-methoxyphenoxy)-4-methylheptanoic acid pyridin-2-ylmethyl ester | 671799-04-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4S,5R)-5-(tert-butyldimethylsilyloxy)-7-(4-methoxyphenoxy)-4-methylheptanoic acid pyridin-2-ylmethyl ester
• 英文别名: pyridin-2-ylmethyl (4S,5R)-5-[tert-butyl(dimethyl)silyl]oxy-7-(4-methoxyphenoxy)-4-methylheptanoate
• CAS: 671799-04-5
• 化学式: C₂₇H₄₁NO₅Si
• 分子量: 487.712
• InChiKey: AGWCOXPNSNZKSB-SQJMNOBHSA-N

物化性质

• 沸点：
  551.4±50.0 °C(Predicted)
• 密度：
  1.040±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.41
• 重原子数：
  34
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S,5R)-5-(tert-butyldimethylsilyloxy)-7-(4-methoxyphenoxy)-4-methylheptanoic acid pyridin-2-ylmethyl ester 在 sodium hydride 、 lithium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.75h， 生成 (2S,4R,5S)-5-(tert-butyldimethylsilyloxy)-7-(4-methoxyphenoxy)-2,4-dimethylheptanoic acid [(1S,2S)-(2-hydroxy-1-methyl-2-phenylethyl)]methylamide
  参考文献：
  名称：

  Synthesis of the C16−C35 Fragment of Integramycin Using Olefin Hydroesterification as a Linchpin Reaction

  摘要：

  The spiroketal unit of the HIV-integrase inhibitor integramycin has been prepared in an efficient and convergent manner. Key steps in this sequence include the use of ruthenium-mediated hydroesterification reactions of homoallylic alcohols and silyl ethers, and a C,O-dianionic addition into a lactone provides the spiroketal while minimizing protecting group manipulations.

  DOI：

  10.1021/ol036339i
• 作为产物：
  描述：

  1-(but-3-en-1-yloxy)-4-methoxybenzene 在 2,6-二甲基吡啶 、 十二羰基三钌 、 三氯一茂钛 、 (4S,5S)-(2,2-二甲基-1,3-二氧戊环-4,5-二基)双(二苯基甲醇) 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 24.33h， 生成 (4S,5R)-5-(tert-butyldimethylsilyloxy)-7-(4-methoxyphenoxy)-4-methylheptanoic acid pyridin-2-ylmethyl ester
  参考文献：
  名称：

  Synthesis of the C16−C35 Fragment of Integramycin Using Olefin Hydroesterification as a Linchpin Reaction

  摘要：

  The spiroketal unit of the HIV-integrase inhibitor integramycin has been prepared in an efficient and convergent manner. Key steps in this sequence include the use of ruthenium-mediated hydroesterification reactions of homoallylic alcohols and silyl ethers, and a C,O-dianionic addition into a lactone provides the spiroketal while minimizing protecting group manipulations.

  DOI：

  10.1021/ol036339i

文献信息

• Synthesis of the C16−C35 Fragment of Integramycin Using Olefin Hydroesterification as a Linchpin Reaction
  作者：Lijun Wang、Paul E. Floreancig

  DOI：10.1021/ol036339i

  日期：2004.2.1

  The spiroketal unit of the HIV-integrase inhibitor integramycin has been prepared in an efficient and convergent manner. Key steps in this sequence include the use of ruthenium-mediated hydroesterification reactions of homoallylic alcohols and silyl ethers, and a C,O-dianionic addition into a lactone provides the spiroketal while minimizing protecting group manipulations.