(1S,2S)-1-[3,5-bis(tert-butyldimethylsilyloxy)phenyl]-2-methyl-4-phenylsulfanylbutan-1-ol | 671798-74-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2S)-1-[3,5-bis(tert-butyldimethylsilyloxy)phenyl]-2-methyl-4-phenylsulfanylbutan-1-ol
• 英文别名: (1S,2S)-1-[3,5-bis[[tert-butyl(dimethyl)silyl]oxy]phenyl]-2-methyl-4-phenylsulfanylbutan-1-ol
• CAS: 671798-74-6
• 化学式: C₂₉H₄₈O₃SSi₂
• 分子量: 532.935
• InChiKey: OKGVHASWPKTCDC-CUNXSJBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.31
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  64
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2S)-1-[3,5-bis(tert-butyldimethylsilyloxy)phenyl]-2-methyl-4-phenylsulfanylbutan-1-ol 在 正丁基锂 、 ammonium cerium(IV) nitrate 、 LiDBB 作用下， 以 四氢呋喃 、 正己烷 、 水 、 乙腈 为溶剂， 反应 1.87h， 生成 2-{(2R,3S,5S,6R,8S,9S)-8-[3,5-bis(tert-butyldimethylsilyloxy)phenyl]-3,5,9-trimethyl-1,7-dioxaspiro[5.5]undec-2-yl}ethanol
  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：

  3,5-bis(tert-butyldimethylsilyloxy)benzaldehyde 在 三氯一茂钛 、 偶氮二异丁腈 、 (4S,5S)-(2,2-二甲基-1,3-二氧戊环-4,5-二基)双(二苯基甲醇) 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 15.5h， 生成 (1S,2S)-1-[3,5-bis(tert-butyldimethylsilyloxy)phenyl]-2-methyl-4-phenylsulfanylbutan-1-ol
  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.