(S)-1-((2S,6S,7S,10R)-7-Isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-2-yl)-3,3-dimethyl-butan-2-ol | 263711-61-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (S)-1-((2S,6S,7S,10R)-7-Isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-2-yl)-3,3-dimethyl-butan-2-ol
• 英文别名: (2S)-3,3-dimethyl-1-[(4S,6S,8R,11S)-8-methyl-11-propan-2-yl-1,5-dioxaspiro[5.5]undecan-4-yl]butan-2-ol
• CAS: 263711-61-1
• 化学式: C₁₉H₃₆O₃
• 分子量: 312.493
• InChiKey: AZJYTHJIQVJMBV-QSUVVDIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-((2S,6S,7S,10R)-7-Isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-2-yl)-3,3-dimethyl-butan-2-ol 在 sodium hydroxide 、 potassium tert-butylate 、 双氧水 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.67h， 生成 3-[(S)-1-((2S,6S,7S,10R)-7-Isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-2-ylmethyl)-2,2-dimethyl-propoxy]-propionaldehyde
  参考文献：
  名称：

  Role of the A-Ring of Bryostatin Analogues in PKC Binding:  Synthesis and Initial Biological Evaluation of New A-Ring-Modified Bryologs

  摘要：

  The syntheses of three newly designed bryostatin analogues are reported. These simplified analogues, which lack the A-ring present in the natural product but possess differing groups at C9, were obtained using a divergent approach from a common intermediate. All three analogues exhibit potent, single-digit nanomolar affinity to protein kinase C.

  DOI：

  10.1021/ol0504650
• 作为产物：
  描述：

  (R)-1-((2S,6S,7S,10R)-7-Isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-2-yl)-3,3-dimethyl-butan-2-ol 在 sodium tetrahydroborate 、 cerium(III) chloride 、 四丙基高钌酸铵 、 4 A molecular sieve 、 N-甲基吗啉氧化物 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 (S)-1-((2S,6S,7S,10R)-7-Isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-2-yl)-3,3-dimethyl-butan-2-ol
  参考文献：
  名称：

  Role of the A-Ring of Bryostatin Analogues in PKC Binding:  Synthesis and Initial Biological Evaluation of New A-Ring-Modified Bryologs

  摘要：

  The syntheses of three newly designed bryostatin analogues are reported. These simplified analogues, which lack the A-ring present in the natural product but possess differing groups at C9, were obtained using a divergent approach from a common intermediate. All three analogues exhibit potent, single-digit nanomolar affinity to protein kinase C.

  DOI：

  10.1021/ol0504650

文献信息

• Synthesis and biological evaluation of bryostatin analogues: the role of the A-ring
  作者：Paul A Wender、Blaise Lippa

  DOI：10.1016/s0040-4039(99)02195-4

  日期：2000.2

  of simplified bryostatin analogues are synthesized through an optimized esterification–macrotransacetalization strategy. This family incorporates both an ester linkage between C5 and C9 in addition to a C9 t-butyl substituent to mimic the bryostatin A-ring. Importantly, a free C7 alcohol is revealed late in the synthesis, allowing access to numerous C7 derivatized analogues.

  通过优化的酯化-宏观反缩醛化策略合成了简化的苔藓抑素类似物新家族的第一个生物活性成员和关键中间体。该家族除C9叔丁基取代基外还结合了C5和C9之间的酯键，以模拟bryostatin A-环。重要的是，在合成后期发现了游离的C7醇，从而可以使用多种C7衍生的类似物。
• Role of the A-Ring of Bryostatin Analogues in PKC Binding:  Synthesis and Initial Biological Evaluation of New A-Ring-Modified Bryologs
  作者：Paul A. Wender、Michael O. Clarke、Joshua C. Horan

  DOI：10.1021/ol0504650

  日期：2005.5.1

  The syntheses of three newly designed bryostatin analogues are reported. These simplified analogues, which lack the A-ring present in the natural product but possess differing groups at C9, were obtained using a divergent approach from a common intermediate. All three analogues exhibit potent, single-digit nanomolar affinity to protein kinase C.