(2R,3S,5S,6R,8S,9S)-8-[3,5-bis(tert-butyldimethylsilyloxy)phenyl]-2-[2-(4-methoxyphenoxy)ethyl]-3,5,9-trimethyl-1,7-dioxaspiro[5.5]undecane | 671798-94-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,3S,5S,6R,8S,9S)-8-[3,5-bis(tert-butyldimethylsilyloxy)phenyl]-2-[2-(4-methoxyphenoxy)ethyl]-3,5,9-trimethyl-1,7-dioxaspiro[5.5]undecane
• 英文别名: tert-butyl-[3-[tert-butyl(dimethyl)silyl]oxy-5-[(2S,3S,6R,8R,9S,11S)-8-[2-(4-methoxyphenoxy)ethyl]-3,9,11-trimethyl-1,7-dioxaspiro[5.5]undecan-2-yl]phenoxy]-dimethylsilane
• CAS: 671798-94-0
• 化学式: C₃₉H₆₄O₆Si₂
• 分子量: 685.105
• InChiKey: FKEJOMLXLZUIGK-JBWNCATOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.18
• 重原子数：
  47
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S,5S,6R,8S,9S)-8-[3,5-bis(tert-butyldimethylsilyloxy)phenyl]-2-[2-(4-methoxyphenoxy)ethyl]-3,5,9-trimethyl-1,7-dioxaspiro[5.5]undecane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以66%的产率得到5-{(2S,3S,6R,8R,9S,11S)-8-[2-(4-methoxyphenoxy)ethyl]-3,9,11-trimethyl-1,7-dioxaspiro[5.5]undec-2-yl}benzene-1,3-diol
  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 十二羰基三钌 咪唑 、 正丁基锂 、 LiDBB 、 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 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 44.08h， 生成 (2R,3S,5S,6R,8S,9S)-8-[3,5-bis(tert-butyldimethylsilyloxy)phenyl]-2-[2-(4-methoxyphenoxy)ethyl]-3,5,9-trimethyl-1,7-dioxaspiro[5.5]undecane
  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.