11β,18,19,21-Tetrahydroxypregn-5-ene-3,20-dione-di-(ethylene ketal) | 110987-90-1

• 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: 11β,18,19,21-Tetrahydroxypregn-5-ene-3,20-dione-di-(ethylene ketal)
• CAS: 110987-90-1
• 化学式: C₂₅H₃₈O₈
• 分子量: 466.572
• InChiKey: XQBBBYNCGRSWQK-KMQZPWIOSA-N

反应信息

• 作为反应物：
  描述：

  11β,18,19,21-Tetrahydroxypregn-5-ene-3,20-dione-di-(ethylene ketal) 在 高氯酸 作用下， 以 吡啶 、 溶剂黄146 为溶剂， 反应 20.17h， 生成 11β,18,19,21-Tetrahydroxypregn-4-ene-3,20-dione 18,19,21-triacetate
  参考文献：
  名称：

  Synthesis of 18,19-dihydroxycorticosterone

  摘要：

  A four-step synthesis of 18,19-dihydroxycorticosterone 5c, starting with 19,21-dihydroxy-3,20-dioxopregn-5-ene-18,11 beta-lactone-di-(ethylene ketal) 2, is presented. Reduction of 2 with sodium aluminum bis-(methoxyethoxy)hydride gave 11 beta,18,19,21-tetrahydroxy-pregn-5-ene-3,20-dione-di-(ethylene ketal) 3a. Acetylation furnished the corresponding 18,19,21-triacetate 3b, which on treatment with a mixture of perchloric and acetic acids gave 18,19-dihydroxycorticosterone 18,19,21-triacetate 4b. Mild saponification yielded the title compound which, on the basis of ir and nmr spectra, exists as one C-20 isomer of the hemiacetal structure 5c. Periodate oxidation of 5c gave the expected 11 beta, 19-dihydroxy-3-oxoandrost-4-ene-17 beta, 18-carbolactone 6b.

  DOI：

  10.1016/0039-128x(86)90089-9
• 作为产物：
  描述：

  19,21-dihydroxy-3,20-dioxopregn-5-ene-18,11β-lactone-di-(ethylene ketal) 在 70percent SAMH 作用下， 以 苯 为溶剂， 反应 0.67h， 以348 mg的产率得到11β,18,19,21-Tetrahydroxypregn-5-ene-3,20-dione-di-(ethylene ketal)
  参考文献：
  名称：

  Synthesis of 18,19-dihydroxycorticosterone

  摘要：

  A four-step synthesis of 18,19-dihydroxycorticosterone 5c, starting with 19,21-dihydroxy-3,20-dioxopregn-5-ene-18,11 beta-lactone-di-(ethylene ketal) 2, is presented. Reduction of 2 with sodium aluminum bis-(methoxyethoxy)hydride gave 11 beta,18,19,21-tetrahydroxy-pregn-5-ene-3,20-dione-di-(ethylene ketal) 3a. Acetylation furnished the corresponding 18,19,21-triacetate 3b, which on treatment with a mixture of perchloric and acetic acids gave 18,19-dihydroxycorticosterone 18,19,21-triacetate 4b. Mild saponification yielded the title compound which, on the basis of ir and nmr spectra, exists as one C-20 isomer of the hemiacetal structure 5c. Periodate oxidation of 5c gave the expected 11 beta, 19-dihydroxy-3-oxoandrost-4-ene-17 beta, 18-carbolactone 6b.

  DOI：

  10.1016/0039-128x(86)90089-9