(20S,23Z,25Z)-23,26-epoxy-6β-methoxy-3α,5-cyclo-27-nor-5α-cholesta-23,25-dien-22-one | 140463-94-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (20S,23Z,25Z)-23,26-epoxy-6β-methoxy-3α,5-cyclo-27-nor-5α-cholesta-23,25-dien-22-one
• CAS: 140463-94-1
• 化学式: C₂₇H₃₈O₃
• 分子量: 410.597
• InChiKey: WUTIJCBQLFGIQQ-SUBPJVIOSA-N

反应信息

• 作为反应物：
  描述：

  (20S,23Z,25Z)-23,26-epoxy-6β-methoxy-3α,5-cyclo-27-nor-5α-cholesta-23,25-dien-22-one 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 生成 (1S,2S)-1-Furan-2-yl-2-((3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-propan-1-ol 、 (1R,2S)-1-Furan-2-yl-2-((3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-propan-1-ol
  参考文献：
  名称：

  A facile construction of withanolide side chains: synthesis of minabeolide-3

  摘要：

  A stereocontrolled construction of withanolide side chains, withanolide R-type 17, and 27-deoxywithaferin A-type 21, was accomplished from 20-carboxaldehyde 6. The key features of the construction are based on the stereoselective synthesis of the furylcarbinol 12 and its transformation into pyranone derivatives. Synthesis of minabeolide-3 28 was achieved from the key intermediate 18.

  DOI：

  10.1021/jo00036a032
• 作为产物：
  描述：

  (1R,2S)-1-Furan-2-yl-2-((3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-propan-1-ol 在 Celite 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以70.9%的产率得到(20S,23Z,25Z)-23,26-epoxy-6β-methoxy-3α,5-cyclo-27-nor-5α-cholesta-23,25-dien-22-one
  参考文献：
  名称：

  A facile construction of withanolide side chains: synthesis of minabeolide-3

  摘要：

  A stereocontrolled construction of withanolide side chains, withanolide R-type 17, and 27-deoxywithaferin A-type 21, was accomplished from 20-carboxaldehyde 6. The key features of the construction are based on the stereoselective synthesis of the furylcarbinol 12 and its transformation into pyranone derivatives. Synthesis of minabeolide-3 28 was achieved from the key intermediate 18.

  DOI：

  10.1021/jo00036a032