(3S)-3-[tert-butyl(diphenyl)silyl]oxy-4-[(2S,6R)-6-[(2S)-2-triethylsilyloxy-4-(trimethylsilylmethyl)pent-4-enyl]oxan-2-yl]butan-1-ol | 1028456-20-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (3S)-3-[tert-butyl(diphenyl)silyl]oxy-4-[(2S,6R)-6-[(2S)-2-triethylsilyloxy-4-(trimethylsilylmethyl)pent-4-enyl]oxan-2-yl]butan-1-ol
• CAS: 1028456-20-3
• 化学式: C₄₀H₆₈O₄Si₃
• 分子量: 697.234
• InChiKey: CUMGMRRPNYKRLN-NBRFXYHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.71
• 重原子数：
  47
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S)-3-[tert-butyl(diphenyl)silyl]oxy-4-[(2S,6R)-6-[(2S)-2-triethylsilyloxy-4-(trimethylsilylmethyl)pent-4-enyl]oxan-2-yl]butan-1-ol 在 四丙基高钌酸铵 4 A molecular sieve 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成
  参考文献：
  名称：

  Efficient Synthetic Access to a New Family of Highly Potent Bryostatin Analogues via a Prins-Driven Macrocyclization Strategy

  摘要：

  The step-economical synthesis of a new class of bryostatin analogues that contain the complete oxycarbocyclic core ring system of the bryostatin natural products is reported. These agents are convergently assembled via a highly efficient, functional-group-tolerant, and stereoselective Prins-driven macrocyclization. These tetrahydropyranyl B-ring analogues are among our most potent and efficacious analogues to date, exhibiting nanomolar and picomolar activities in protein kinase C affinity assays as well as in cellular antiproliferation assays.

  DOI：

  10.1021/ja8015632
• 作为产物：
  描述：

  tert-butyl-diphenyl-[(2S)-4-phenylmethoxy-1-[(2S,6R)-6-[(2S)-2-triethylsilyloxy-4-(trimethylsilylmethyl)pent-4-enyl]oxan-2-yl]butan-2-yl]oxysilane 在 naphthalen-1-yl-lithium 作用下， 以 四氢呋喃 为溶剂， 以93%的产率得到(3S)-3-[tert-butyl(diphenyl)silyl]oxy-4-[(2S,6R)-6-[(2S)-2-triethylsilyloxy-4-(trimethylsilylmethyl)pent-4-enyl]oxan-2-yl]butan-1-ol
  参考文献：
  名称：

  Efficient Synthetic Access to a New Family of Highly Potent Bryostatin Analogues via a Prins-Driven Macrocyclization Strategy

  摘要：

  The step-economical synthesis of a new class of bryostatin analogues that contain the complete oxycarbocyclic core ring system of the bryostatin natural products is reported. These agents are convergently assembled via a highly efficient, functional-group-tolerant, and stereoselective Prins-driven macrocyclization. These tetrahydropyranyl B-ring analogues are among our most potent and efficacious analogues to date, exhibiting nanomolar and picomolar activities in protein kinase C affinity assays as well as in cellular antiproliferation assays.

  DOI：

  10.1021/ja8015632

文献信息

• Efficient Synthetic Access to a New Family of Highly Potent Bryostatin Analogues via a Prins-Driven Macrocyclization Strategy
  作者：Paul A. Wender、Brian A. DeChristopher、Adam J. Schrier

  DOI：10.1021/ja8015632

  日期：2008.5.1

  The step-economical synthesis of a new class of bryostatin analogues that contain the complete oxycarbocyclic core ring system of the bryostatin natural products is reported. These agents are convergently assembled via a highly efficient, functional-group-tolerant, and stereoselective Prins-driven macrocyclization. These tetrahydropyranyl B-ring analogues are among our most potent and efficacious analogues to date, exhibiting nanomolar and picomolar activities in protein kinase C affinity assays as well as in cellular antiproliferation assays.