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

• 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''R)-N,N-diisopropyl-{7,7-dimethyl-2-spiro-2'-[5'-(2''-carbomethoxy-1''-methyl)ethyl-1',3'-dioxolane-4'-one]}bicyclo[2.2.1]hept-1-ylmethanesulfonamide
• 英文别名: methyl (3R)-3-[(1'S,2S,4R,4'R)-1'-[di(propan-2-yl)sulfamoylmethyl]-7',7'-dimethyl-5-oxospiro[1,3-dioxolane-2,2'-bicyclo[2.2.1]heptane]-4-yl]butanoate
• 化学式: C₂₃H₃₉NO₇S
• 分子量: 473.631
• InChiKey: VYMFEHKXDNGKOD-DKDCZHCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 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''R)-N,N-diisopropyl-{7,7-dimethyl-2-spiro-2'-[5'-(2''-carbomethoxy-1''-methyl)ethyl-1',3'-dioxolane-4'-one]}bicyclo[2.2.1]hept-1-ylmethanesulfonamide 在 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 生成 (2R,3R)-N-benzyl-3-methyl-5-oxotetrahydrofuran-2-carboxamide
  参考文献：
  名称：

  Formal asymmetric synthesis of (+)-tofacitinib

  摘要：

  Tofacitinib is an efficient and selective Janus kinase 3 (JAK3) inhibitor, and is used as an immunosuppressant drug for the treatment of rheumatoid arthritis and transplant patients. Herein we report a concise formal asymmetric synthesis of tofacitinib from homochiral 1,3-dioxolanone 10b, which was elaborated through a highly stereoselective Michael addition followed by solvent-free removal of the chiral auxiliary and ring cyclization to furnish chiral imide 8. The preparation of tofacitinib's precursor 16 could be obtained after reduction of 8 followed by sequential oxidation, reductive amination and SNAr reactions. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.11.013
• 作为产物：
  描述：

  巴豆酸甲酯 、 (1S,2S)-N,N-diisopropyl [2-spiro-2'-(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82%的产率得到(1S,2S,5'R,1''R)-N,N-diisopropyl-{7,7-dimethyl-2-spiro-2'-[5'-(2''-carbomethoxy-1''-methyl)ethyl-1',3'-dioxolane-4'-one]}bicyclo[2.2.1]hept-1-ylmethanesulfonamide
  参考文献：
  名称：

  摘要：

  DOI：

  10.5555/ol0069507