(2S,4S,6S,8R)-2-[(2S,4S)-6-[tert-butyl(diphenyl)silyl]oxy-2,4-bis[tri(propan-2-yl)silyloxy]hexyl]-8-ethenyl-3,3-dimethyl-4-triethylsilyloxy-1,7-dioxaspiro[5.5]undecan-10-one | 1322588-85-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4S,6S,8R)-2-[(2S,4S)-6-[tert-butyl(diphenyl)silyl]oxy-2,4-bis[tri(propan-2-yl)silyloxy]hexyl]-8-ethenyl-3,3-dimethyl-4-triethylsilyloxy-1,7-dioxaspiro[5.5]undecan-10-one
• CAS: 1322588-85-1
• 化学式: C₅₉H₁₀₄O₇Si₄
• 分子量: 1037.81
• InChiKey: SCLLGALZJLWMCM-BZAHTJPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.69
• 重原子数：
  70
• 可旋转键数：
  27
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (三甲基硅基)乙酸甲酯 、 (2S,4S,6S,8R)-2-[(2S,4S)-6-[tert-butyl(diphenyl)silyl]oxy-2,4-bis[tri(propan-2-yl)silyloxy]hexyl]-8-ethenyl-3,3-dimethyl-4-triethylsilyloxy-1,7-dioxaspiro[5.5]undecan-10-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 、 methyl (2E)-2-[(2S,4S,6R,8R)-2-[(2S,4S)-6-[tert-butyl(diphenyl)silyl]oxy-2,4-bis[tri(propan-2-yl)silyloxy]hexyl]-8-ethenyl-3,3-dimethyl-4-triethylsilyloxy-1,7-dioxaspiro[5.5]undecan-10-ylidene]acetate
  参考文献：
  名称：

  Toward the Total Synthesis of Bryostatin 11: Stereoselective Construction of the C13-Exocyclic Enoate in the C1–C16 Fragment

  摘要：

  We have utilized a spiroketal template in an approach to the C1-C16 fragment of bryostatin. The stereoselective construction of an exocyclic enoate at C13 and insertion of a vinyl group on C15 were accomplished by using Peterson-Yamamoto olefination and copper-catalyzed addition of vinyl magnesium bromide, respectively.

  DOI：

  10.1080/00397911.2010.516462
• 作为产物：
  描述：

  、 乙烯基溴化镁 在 tetrakis{iodo(tributylphosphine)copper(I)} 作用下， 反应 0.5h， 以85%的产率得到(2S,4S,6S,8R)-2-[(2S,4S)-6-[tert-butyl(diphenyl)silyl]oxy-2,4-bis[tri(propan-2-yl)silyloxy]hexyl]-8-ethenyl-3,3-dimethyl-4-triethylsilyloxy-1,7-dioxaspiro[5.5]undecan-10-one
  参考文献：
  名称：

  Toward the Total Synthesis of Bryostatin 11: Stereoselective Construction of the C13-Exocyclic Enoate in the C1–C16 Fragment

  摘要：

  We have utilized a spiroketal template in an approach to the C1-C16 fragment of bryostatin. The stereoselective construction of an exocyclic enoate at C13 and insertion of a vinyl group on C15 were accomplished by using Peterson-Yamamoto olefination and copper-catalyzed addition of vinyl magnesium bromide, respectively.

  DOI：

  10.1080/00397911.2010.516462

文献信息

• Toward the Total Synthesis of Bryostatin 11: Stereoselective Construction of the C13-Exocyclic Enoate in the C1–C16 Fragment
  作者：Kyoko Nakagawa-Goto、Michael T. Crimmins

  DOI：10.1080/00397911.2010.516462

  日期：2011.10.15

  We have utilized a spiroketal template in an approach to the C1-C16 fragment of bryostatin. The stereoselective construction of an exocyclic enoate at C13 and insertion of a vinyl group on C15 were accomplished by using Peterson-Yamamoto olefination and copper-catalyzed addition of vinyl magnesium bromide, respectively.