5-(benzenesulfonyl)-1-<(tert-butyldimethylsilyl)oxy>-3,8,12,16-tetramethyl-3(E),7(E),11(E),15-heptadecatetraene | 140176-40-5

• 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: 5-(benzenesulfonyl)-1-<(tert-butyldimethylsilyl)oxy>-3,8,12,16-tetramethyl-3(E),7(E),11(E),15-heptadecatetraene
• 英文别名: 5-(benzenesulfonyl)-1-[(tert-butyldimethylsilyl)oxy]-3,8,12,16-tetramethyl-3(E),7(E),11(E),15-heptadecatetraene；[(3E,7E,11E)-5-(benzenesulfonyl)-3,8,12,16-tetramethylheptadeca-3,7,11,15-tetraenoxy]-tert-butyl-dimethylsilane
• CAS: 140176-40-5
• 化学式: C₃₃H₅₄O₃SSi
• 分子量: 558.941
• InChiKey: BSWFUKWGDAXSGF-GXZPWXFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.0
• 重原子数：
  38.0
• 可旋转键数：
  15.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-(benzenesulfonyl)-1-<(tert-butyldimethylsilyl)oxy>-3,8,12,16-tetramethyl-3(E),7(E),11(E),15-heptadecatetraene 在 四丁基氟化铵 、 lithium 、 乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.58h， 生成 3,8,12,16-tetramethyl-3(E),7(E),11(E),15-heptadecatetraen-1-ol
  参考文献：
  名称：

  Synthesis of inhibitors of 2,3-oxidosqualene-lanosterol cyclase: conjugate addition of organocuprates to N-(carbobenzyloxy)-3-carbomethoxy-5,6-dihydro-4-pyridone.

  摘要：

  Synthesis of ammonium ion analogues of the first cationic intermediate, 5, presumed to be formed during the cyclization of 2,3-oxidosqualene by 2,3-oxidosqualene-lanosterol cyclase are reported. The required 2,3-substituted-4-piperidinols are prepared by conjugate addition of higher order alkyl (2-thienyl)(cyano)cuprates to 1-(carbobenzyloxy)-3-carbomethoxy-5,6-dihydro-4-pyridone. The nitrogen protecting group (carbobenzyloxy) is key to the synthesis in that it allows the conjugate addition to proceed in high yield and is easily converted to the required N-methyl group in the final products. The key terpenoid side chain appended to C-2 of the piperidinols was constructed from homofarnesyl bromide and 1,5-difunctionalized homoisopentenyl derivatives prepared by zirconium-catalyzed carboalumination of protected 1-butyn-4-ol.

  DOI：

  10.1021/jo00036a008
• 作为产物：
  描述：

  ethyl (E)-5-((tert-butyldimethylsilyl)oxy)-3-methylpent-2-enoate 在 正丁基锂 、 N-chlorosuccinimide-dimethyl sulfide 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 5-(benzenesulfonyl)-1-<(tert-butyldimethylsilyl)oxy>-3,8,12,16-tetramethyl-3(E),7(E),11(E),15-heptadecatetraene
  参考文献：
  名称：

  Synthesis of inhibitors of 2,3-oxidosqualene-lanosterol cyclase: conjugate addition of organocuprates to N-(carbobenzyloxy)-3-carbomethoxy-5,6-dihydro-4-pyridone.

  摘要：

  Synthesis of ammonium ion analogues of the first cationic intermediate, 5, presumed to be formed during the cyclization of 2,3-oxidosqualene by 2,3-oxidosqualene-lanosterol cyclase are reported. The required 2,3-substituted-4-piperidinols are prepared by conjugate addition of higher order alkyl (2-thienyl)(cyano)cuprates to 1-(carbobenzyloxy)-3-carbomethoxy-5,6-dihydro-4-pyridone. The nitrogen protecting group (carbobenzyloxy) is key to the synthesis in that it allows the conjugate addition to proceed in high yield and is easily converted to the required N-methyl group in the final products. The key terpenoid side chain appended to C-2 of the piperidinols was constructed from homofarnesyl bromide and 1,5-difunctionalized homoisopentenyl derivatives prepared by zirconium-catalyzed carboalumination of protected 1-butyn-4-ol.

  DOI：

  10.1021/jo00036a008

文献信息

• Synthesis of inhibitors of 2,3-oxidosqualene-lanosterol cyclase: conjugate addition of organocuprates to N-(carbobenzyloxy)-3-carbomethoxy-5,6-dihydro-4-pyridone.
  作者：Dharmpal S. Dodd、Allan C. Oehlschlager

  DOI：10.1021/jo00036a008

  日期：1992.5

  Synthesis of ammonium ion analogues of the first cationic intermediate, 5, presumed to be formed during the cyclization of 2,3-oxidosqualene by 2,3-oxidosqualene-lanosterol cyclase are reported. The required 2,3-substituted-4-piperidinols are prepared by conjugate addition of higher order alkyl (2-thienyl)(cyano)cuprates to 1-(carbobenzyloxy)-3-carbomethoxy-5,6-dihydro-4-pyridone. The nitrogen protecting group (carbobenzyloxy) is key to the synthesis in that it allows the conjugate addition to proceed in high yield and is easily converted to the required N-methyl group in the final products. The key terpenoid side chain appended to C-2 of the piperidinols was constructed from homofarnesyl bromide and 1,5-difunctionalized homoisopentenyl derivatives prepared by zirconium-catalyzed carboalumination of protected 1-butyn-4-ol.