(1S,2S,5'R,1''S)-N,N-diisopropyl-{7,7-dimethyl-2-spiro-2'-[5',5'-(2''-carbomethoxy-1''-methyl)ethylmethyl-1',3'-dioxolane-4'-one]}bicyclo[2.2.1]hept-1-ylmethanesulfonamide | 337365-53-4

• 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: (1S,2S,5'R,1''S)-N,N-diisopropyl-{7,7-dimethyl-2-spiro-2'-[5',5'-(2''-carbomethoxy-1''-methyl)ethylmethyl-1',3'-dioxolane-4'-one]}bicyclo[2.2.1]hept-1-ylmethanesulfonamide
• 英文别名: methyl (3S)-3-[(1'S,2S,4R,4'R)-1'-[di(propan-2-yl)sulfamoylmethyl]-4,7',7'-trimethyl-5-oxospiro[1,3-dioxolane-2,2'-bicyclo[2.2.1]heptane]-4-yl]butanoate
• CAS: 337365-53-4
• 化学式: C₂₄H₄₁NO₇S
• 分子量: 487.658
• InChiKey: JBTLXCSDWKQKRV-ASSVPYPDSA-N

物化性质

• 沸点：
  557.1±48.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1S,2S,5'R,1''S)-N,N-diisopropyl-{7,7-dimethyl-2-spiro-2'-[5',5'-(2''-carbomethoxy-1''-methyl)ethylmethyl-1',3'-dioxolane-4'-one]}bicyclo[2.2.1]hept-1-ylmethanesulfonamide 在 lithium diisopropyl amide 、 2-(Phenylsulfonyl)-3-phenyloxaziridin 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 25.41h， 以82%的产率得到(1S,2S,5'R,1''S,2''S)-N,N-diisopropyl{2-spiro-2'-[5'-(2''-hydroxy-2''-carbomethoxy-1''-methylethyl)-5'-methyl-1',3'-dioxolane-4'-one]-7,7-dimethylbicyclo[2.2.1]hept-1-yl}methanesulfonamide
  参考文献：
  名称：

  Stereoselective Michael-alkylation and Michael-oxidation reactions of chiral 1,3-dioxolanones

  摘要：

  A highly diastereoselective Michael-alkylation/oxidation methodology has been developed for the synthesis of optically active alpha-hydroxy-1,5-diester subunits. Inverse stereochemistry at the C-2' position could be achieved by using a Michael acceptor equipped with a suitable group followed by a highly stereoselective protonation. This methodology has been applied to the enantioselective synthesis of the upper fragment of (+)-retusine. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.05.002
• 作为产物：
  描述：

  巴豆酸甲酯 、 (1S,2S,5'S)-N,N-diisopropyl [2-spiro-2'-(5'-methyl-1',3'-dioxolane-4'-one)-7,7-dimethylbicyclo[2.2.1]hept-1-yl]methanesulfonamide 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.5h， 以92%的产率得到(1S,2S,5'R,1''S)-N,N-diisopropyl-{7,7-dimethyl-2-spiro-2'-[5',5'-(2''-carbomethoxy-1''-methyl)ethylmethyl-1',3'-dioxolane-4'-one]}bicyclo[2.2.1]hept-1-ylmethanesulfonamide
  参考文献：
  名称：

  摘要：

  DOI：

  10.5555/ol0069507

文献信息

• Stereoselective Michael-alkylation and Michael-oxidation reactions of chiral 1,3-dioxolanones
  作者：Hao-Chun Liao、Kuan-Jen Yao、Yi-Chou Tsai、Biing-Jiun Uang

  DOI：10.1016/j.tetasy.2017.05.002

  日期：2017.6

  A highly diastereoselective Michael-alkylation/oxidation methodology has been developed for the synthesis of optically active alpha-hydroxy-1,5-diester subunits. Inverse stereochemistry at the C-2' position could be achieved by using a Michael acceptor equipped with a suitable group followed by a highly stereoselective protonation. This methodology has been applied to the enantioselective synthesis of the upper fragment of (+)-retusine. (C) 2017 Elsevier Ltd. All rights reserved.
• ——
  作者：D.-P. Jang、J.-W. Chang、B.-J. Uang

  DOI：10.5555/ol0069507

  日期：2001.4.5