(1S,3S,7R,11S,15S,17R,21R,23S,25S,E)-17-((R)-1-((benzyloxy)methoxy)ethyl)-21-((tert-butyldiphenylsilyl)oxy)-25-hydroxy-11-methoxy-10,10,26,26-tetramethyl-5-methylene-18,27,28,29-tetraoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-ene-12,19-dione | 1383605-16-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (1S,3S,7R,11S,15S,17R,21R,23S,25S,E)-17-((R)-1-((benzyloxy)methoxy)ethyl)-21-((tert-butyldiphenylsilyl)oxy)-25-hydroxy-11-methoxy-10,10,26,26-tetramethyl-5-methylene-18,27,28,29-tetraoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-ene-12,19-dione
• CAS: 1383605-16-0
• 化学式: C₅₇H₇₈O₁₁Si
• 分子量: 967.325
• InChiKey: WGWIRPGCYTWHBU-IWIOQYRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.32
• 重原子数：
  69.0
• 可旋转键数：
  11.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  128.21
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  三乙基氯硅烷 、 (1S,3S,7R,11S,15S,17R,21R,23S,25S,E)-17-((R)-1-((benzyloxy)methoxy)ethyl)-21-((tert-butyldiphenylsilyl)oxy)-25-hydroxy-11-methoxy-10,10,26,26-tetramethyl-5-methylene-18,27,28,29-tetraoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-ene-12,19-dione 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以93%的产率得到(1S,3S,7R,11S,15S,17R,21R,23R,25S,E)-17-((R)-1-((benzyloxy)methoxy)ethyl)-21-((tert-butyldiphenyl silyl)oxy)-11-methoxy-10,10,26,26-tetramethyl-5-methylene-25-((triethylsilyl)oxy)-18,27,28,29-tetraoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-ene-12,19-dione
  参考文献：
  名称：

  Role of the C8 gem-dimethyl group of bryostatin 1 on its unique pattern of biological activity

  摘要：

  The role of the C-8 gem-dimethyl group in the A-ring of bryostatin 1 has been examined through chemical synthesis and biological evaluation of a new analogue. Assays for biological function using U937, K562, and MV4-11 cells as well as the profiles for downregulation of PKC isozymes revealed that the presence of this group is not a critical determinant for the unique pattern of biological activity of bryostatin. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.073
• 作为产物：
  描述：

  (2S,4S,6S)-2-(((2S,6R)-6-((E)-3-((2S,6S)-6-((2R,3R)-3-(benzyloxymethoxy)-2-hydroxybutyl)-2-methoxy-3-oxotetrahydro-2H-pyran-2-yl)-3-methylbut-1-enyl)-4-methylenetetrahydro-2H-pyran-2-yl)methyl)-6-(R)-2-(terttertbutyldiphenylsilyloxy)acetate 在 2,4,6-三氯苯甲酰氯 、 potassium carbonate 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 29.5h， 生成 (1S,3S,7R,11S,15S,17R,21R,23S,25S,E)-17-((R)-1-((benzyloxy)methoxy)ethyl)-21-((tert-butyldiphenylsilyl)oxy)-25-hydroxy-11-methoxy-10,10,26,26-tetramethyl-5-methylene-18,27,28,29-tetraoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-ene-12,19-dione
  参考文献：
  名称：

  Role of the C8 gem-dimethyl group of bryostatin 1 on its unique pattern of biological activity

  摘要：

  The role of the C-8 gem-dimethyl group in the A-ring of bryostatin 1 has been examined through chemical synthesis and biological evaluation of a new analogue. Assays for biological function using U937, K562, and MV4-11 cells as well as the profiles for downregulation of PKC isozymes revealed that the presence of this group is not a critical determinant for the unique pattern of biological activity of bryostatin. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.073