(20S)-6β-methoxy-3α,5-cyclo-26,27-bisnor-5α-cholest-23-en-22-one | 431948-57-1

• 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)-6β-methoxy-3α,5-cyclo-26,27-bisnor-5α-cholest-23-en-22-one
• 英文别名: (E,2S)-2-[(1S,2R,5R,7R,8R,10S,11S,14R,15S)-8-methoxy-2,15-dimethyl-14-pentacyclo[8.7.0.02,7.05,7.011,15]heptadecanyl]hex-4-en-3-one
• CAS: 431948-57-1
• 化学式: C₂₆H₄₀O₂
• 分子量: 384.602
• InChiKey: WJAZXJZPQYPTDX-HHZLRCJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (20S)-6β-methoxy-3α,5-cyclo-26,27-bisnor-5α-cholest-23-en-22-one 在 lithium aluminium tetrahydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (22R,23S,24R)/(22R,23R,24S)-6β-methoxy-23,24-epoxy-3α,5-cyclo-26,27-bisnor-5α-cholestan-22-ol
  参考文献：
  名称：

  摘要：

  A biosynthetic precursor of brassinolide, (22R,23R,24S)-24-methyl-3alpha-cholestane-3beta,6alpha,22,23-tetraol was synthesized from Delta(23)-22-keto steroid which was obtained from the corresponding 20-carbonitrile oxide. The side chain was built up by a series of successive transformations: hydride reduction of the initial enone, epoxidation of the allyl-like alcohol, and copper(I) cyanide-catalyzed opening of the 23,24-epoxy ring. The cyclic fragment was completed by opening of the cyclopropane ring with subsequent hydroboration and oxidation of the Delta(5)-bond.

  DOI：

  10.1023/a:1013804119279
• 作为产物：
  描述：

  (20S)-20-[5-(bromomethyl)-4,5-dihydroisoxazol-3-yl]-6β-methoxy-3α,5-cyclo-5α-pregnane 在 镍 偶氮二异丁腈 、 氢气 、 三正丁基氢锡 、 硼酸 、 甲基磺酰氯 作用下， 以 吡啶 、 乙醇 、 乙酸乙酯 、 苯 为溶剂， 反应 13.5h， 生成 (20S)-6β-methoxy-3α,5-cyclo-26,27-bisnor-5α-cholest-23-en-22-one
  参考文献：
  名称：

  摘要：

  Delta(23)-22-Oxo steroids were synthesized via 1,3-dipolar cycloaddition of steroidal nitrile oxides to low-molecular dipolarophiles. Cycloaddition of 2-propynyl bromide to 20-carbonitrile oxide, followed by hydrogenation of the isoxazole derivative thus formed gave 22-enamino-24-keto steroid. The latter was then converted into the target enones via several pathways. Compounds with unnatural configuration of the C-20 atom can also be obtained. Delta(23)-22-Oxo steroids were also synthesized through isoxazole derivatives.

  DOI：

  10.1023/a:1013856103349