5α-Cholest-7-ene-3β,6α,9α,11α-tetrol | 137888-10-9

• 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: 5α-Cholest-7-ene-3β,6α,9α,11α-tetrol
• CAS: 137888-10-9
• 化学式: C₂₇H₄₆O₄
• 分子量: 434.66
• InChiKey: GMLHRFLNILVSQW-PKFHVJCRSA-N

反应信息

• 作为反应物：
  描述：

  5α-Cholest-7-ene-3β,6α,9α,11α-tetrol 在 lead(IV) acetate 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以1.8 mg的产率得到3β,6α-Dihydroxy-9-oxo-9,11-seco-5α-cholest-7-en-11-al
  参考文献：
  名称：

  从海绵上合成的新型9,11-甾醇3β，6α-二羟基-9-氧代9,11-seco-5α-胆固醇7-en-11-al的结构解析和合成。

  摘要：

  从海洋海绵中分离到了一种新型的9,11-甾醇3β，6α-二羟基-9-oxo-9,11-seco-5α-胆固醇7-en-11-al（1），并推导了其结构。通过分析包括1 H NMR COZY和1 H and 13 C相关NMR实验的光谱数据。从7-脱氢胆固醇开始的合成证实了1的结构。

  DOI：

  10.1016/s0040-4020(01)81948-7
• 作为产物：
  描述：

  5α-cholest-7-ene-3β,6α,9α,11α-tetrol-3,6-diacetate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.33h， 以1.5 mg的产率得到5α-Cholest-7-ene-3β,6α,9α,11α-tetrol
  参考文献：
  名称：

  Studies towards the synthesis of polyoxygenated steroids. Reaction of 7,9(11)-diene steroids with RuO4.

  摘要：

  In order to find an entry to C-ring oxygenated steroids, the reaction of ruthenium tetroxide with some Delta(7,9(11))-sterols gas been explored. The reaction has been performed both at -70 degrees C and room temperature using an equimolecular amount of the oxidant and acetone-water as solvent system in the absence of a cooxidant. The change in the temperature conditions moderately affects the yields of the reaction products. When 3 beta,6 alpha- and 3 beta,6 beta-diacetoxy-Delta(7,9(11))-sterols were used the diene system was predominantly attacked at the 9(11)-double bond from the alpha-face of the molecule giving Delta(7)-9 alpha-hydroxy-11-keto- and Delta(7)-9 alpha,11 alpha-dihydroxy-sterols. RuO4 oxidation of cholesta-7,9(11)-dien-3 beta-yl acetate, yielded, in addition to the above oxidation products, minor amounts of three related C-7,C-11 oxigenated 8 alpha,9 alpha-epoxysterols, arising from the oxidation of both double bonds of the diene system. These results, that in part parallel those we recently found on RuO4 oxidation of trisubstituted [Delta(4), Delta(5) and Delta(7)] steroidal alkenes, shed further light on the reactivity of this oxidizing agent which, neverthless, seems far from being completely understood. In addition, our procedure furnishes a reliable route to Delta(7)-9 alpha,11 beta-dihydroxysterols via LiAlH4 reduction of the 11-keto group.

  DOI：

  10.1016/s0040-4020(01)85020-1