(22S)-6β-methoxy-3α,5-cyclo-26,27-bisnor-5α-cholest-23-en-22-ol | 81477-25-0

• 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: (22S)-6β-methoxy-3α,5-cyclo-26,27-bisnor-5α-cholest-23-en-22-ol
• 英文别名: (E,2S,3S)-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-ol
• CAS: 81477-25-0
• 化学式: C₂₆H₄₂O₂
• 分子量: 386.618
• InChiKey: UYSUKTDBJWYXDM-BGDYOUIMSA-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：
  0.92
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (22S)-6β-methoxy-3α,5-cyclo-26,27-bisnor-5α-cholest-23-en-22-ol 在 copper(l) cyanide 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 (22R,23S,24R)-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：

  6β-甲氧基-3α，5-环-5α-孕烷-20α-甲醛 在 正丁基锂 、 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.08h， 生成 (22S)-6β-methoxy-3α,5-cyclo-26,27-bisnor-5α-cholest-23-en-22-ol
  参考文献：
  名称：

  使用砷化物方便地立体选择性合成Castasterone及其类似物

  摘要：

  （2α，3α，22S）-三羟基-5α-胆甾醇-6-one 3和（2α，3α，22R）-三羟基-5α-胆甾醇-6-one 4已经以高的立体选择性合成。关键步骤是将醛5与砷化叶立德偶联，然后进行原位DIBAH还原。第二砷叶立德用于制备关键的烯丙醇中间体15，该中间体允许合成Castasterone 2。

  DOI：

  10.1016/0040-4020(96)00186-x

文献信息

• Takatsuto, Suguru; Watanabe, Tsuyoshi; Fujioka, Shozo, Journal of Chemical Research, Miniprint, 1997, # 4, p. 901 - 924
  作者：Takatsuto, Suguru、Watanabe, Tsuyoshi、Fujioka, Shozo、Sakurai, Akira

  DOI：——

  日期：——
• ——
  作者：V. A. Khripach、V. N. Zhabinskii、N. D. Pavlovskii

  DOI：10.1023/a:1013804119279

  日期：——

  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.
• A convenient stereoselective synthesis of castasterone and its analogues using arsenic ylides
  作者：Frédéric Werner、Gilles Parmentier、Bang Luu、Laurence Dinan

  DOI：10.1016/0040-4020(96)00186-x

  日期：1996.4

  22R)-trihydroxy-5α-cholestan-6-one 4 have been synthesized with high stereoselectivity. The key step is the coupling of the aldehyde 5 with an arsenic ylide, followed by an in situ DIBAH reduction. A second arsenic ylide was used to prepare the key allylic alcohol intermediate 15, which allows the synthesis of castasterone 2.

  （2α，3α，22S）-三羟基-5α-胆甾醇-6-one 3和（2α，3α，22R）-三羟基-5α-胆甾醇-6-one 4已经以高的立体选择性合成。关键步骤是将醛5与砷化叶立德偶联，然后进行原位DIBAH还原。第二砷叶立德用于制备关键的烯丙醇中间体15，该中间体允许合成Castasterone 2。