(1S,6R,10R,11S)-1-[(1S,2R,3R,5R,7S)-5-[(2S,5R,6R,8R,10R)-2-(2-benzyloxy)ethyl-5-methyl-5-(triethylsilyl)oxy-1,7,9-trioxadispiro[5.1.5.2]pentadecan-10-ylmethyl]-2-(tert-butyldimethylsilyl)oxy-3-methyl-6,8-dioxabicyclo[3.2.1]octan-7-yl]-3-(tert-butyldiphenylsilyl)oxymethyl-10,11-dimethyl-8-oxaspiro[5.6]dodec-2-en-7-one | 1075244-28-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,6R,10R,11S)-1-[(1S,2R,3R,5R,7S)-5-[(2S,5R,6R,8R,10R)-2-(2-benzyloxy)ethyl-5-methyl-5-(triethylsilyl)oxy-1,7,9-trioxadispiro[5.1.5.2]pentadecan-10-ylmethyl]-2-(tert-butyldimethylsilyl)oxy-3-methyl-6,8-dioxabicyclo[3.2.1]octan-7-yl]-3-(tert-butyldiphenylsilyl)oxymethyl-10,11-dimethyl-8-oxaspiro[5.6]dodec-2-en-7-one
• 英文别名: (5S,6R,10R,11S)-5-[(1S,2R,3R,5R,7S)-2-[tert-butyl(dimethyl)silyl]oxy-3-methyl-5-[[(4R,6R,8R,10S,13R)-13-methyl-10-(2-phenylmethoxyethyl)-13-triethylsilyloxy-5,7,9-trioxadispiro[5.1.58.26]pentadecan-4-yl]methyl]-6,8-dioxabicyclo[3.2.1]octan-7-yl]-3-[[tert-butyl(diphenyl)silyl]oxymethyl]-10,11-dimethyl-8-oxaspiro[5.6]dodec-3-en-7-one
• CAS: 1075244-28-8
• 化学式: C₇₂H₁₁₀O₁₁Si₃
• 分子量: 1235.92
• InChiKey: JJMQTCGYAMECEJ-XCLDDWRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.74
• 重原子数：
  86
• 可旋转键数：
  22
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (1S,6R,10R,11S)-1-[(1S,2R,3R,5R,7S)-5-[(2S,5R,6R,8R,10R)-2-(2-benzyloxy)ethyl-5-methyl-5-(triethylsilyl)oxy-1,7,9-trioxadispiro[5.1.5.2]pentadecan-10-ylmethyl]-2-(tert-butyldimethylsilyl)oxy-3-methyl-6,8-dioxabicyclo[3.2.1]octan-7-yl]-3-(tert-butyldiphenylsilyl)oxymethyl-10,11-dimethyl-8-oxaspiro[5.6]dodec-2-en-7-one 在 甲酸 、 10% Pd/C 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以81%的产率得到(1S,6R,10R,11S)-1-[(1S,2R,3R,5R,7S)-2-(tert-butyldimethylsilyl)oxy-5-[(2S,5R,6R,8R,10R)-2-(2-hydroxy)ethyl-5-methyl-5-(triethylsilyl)oxy-1,7,9-trioxadispiro[5.1.5.2]pentadecan-10-ylmethyl]-3-methyl-6,8-dioxabicyclo[3.2.1]octan-7-yl]-3-(tert-butyldiphenylsilyl)oxymethyl-10,11-dimethyl-8-oxaspiro[5.6]dodec-2-en-7-one
  参考文献：
  名称：

  品纳毒素A的全合成。

  摘要：

  DOI：

  10.1002/anie.200802729
• 作为产物：
  描述：

  (5S,6R)-5,6-dimethyl-3-methyleneoxepan-2-one 、 (2S,5R,6R,8R,10R)-2-(2-benzyloxy)ethyl-10-[(1S,2R,3R,5R,7S)-2-(tert-butyldimethylsilyl)oxy-[(1E)-3-(tert-butyldiphenylsilyl)oxymethylbuta-1,3-dienyl]-3-methyl-6,8-dioxabicyclo[3.2.1]octan-5-ylmethyl]-5-methyl-5-(triethylsilyl)oxy-1,7,9-trioxadispiro[5.1.5.2]pentadecane 以 对二甲苯 为溶剂， 反应 12.0h， 以35%的产率得到(1S,6R,10R,11S)-1-[(1S,2R,3R,5R,7S)-5-[(2S,5R,6R,8R,10R)-2-(2-benzyloxy)ethyl-5-methyl-5-(triethylsilyl)oxy-1,7,9-trioxadispiro[5.1.5.2]pentadecan-10-ylmethyl]-2-(tert-butyldimethylsilyl)oxy-3-methyl-6,8-dioxabicyclo[3.2.1]octan-7-yl]-3-(tert-butyldiphenylsilyl)oxymethyl-10,11-dimethyl-8-oxaspiro[5.6]dodec-2-en-7-one
  参考文献：
  名称：

  品纳毒素A的全合成。

  摘要：

  DOI：

  10.1002/anie.200802729

文献信息

• Total Synthesis of Pinnatoxin A
  作者：Seiichi Nakamura、Fumiaki Kikuchi、Shunichi Hashimoto

  DOI：10.1002/anie.200802729

  日期：2008.9.1