(20E)-6β-methoxy-3α,5-cyclo-5α-cholest-20(22)-ene | 60084-34-6

• 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: (20E)-6β-methoxy-3α,5-cyclo-5α-cholest-20(22)-ene
• CAS: 60084-34-6
• 化学式: C₂₈H₄₆O
• 分子量: 398.673
• InChiKey: PAVYNCIFSBZYAK-OCOASHRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.65
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (20E)-6β-methoxy-3α,5-cyclo-5α-cholest-20(22)-ene 在 四氧化锇 、 (DHQ)2AQN 作用下， 以 叔丁醇 为溶剂， 以92%的产率得到(2S,3S)-2-((1aR,3aR,3bS,5aS,6S,8aS,8bS,10R,10aR)-10-Methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-6-methyl-heptane-2,3-diol
  参考文献：
  名称：

  Studies on the construction of abutasterone-type and 24-epi-abutasterone-type side chains employing asymmetric dihydroxylation of (E)-20(22),24-cholestadiene

  摘要：

  The synthesis of abutasterone-type side chain, (20R,22R,24S)-20,22,24,25-tetrahydroxy-6 beta-methoxy-3 alpha,5-cyclo-5 alpha-cholestane 4, and 24-epi-abutasterone-type side chain, (20R,22R,24R)-20,22,24,25-tetrahydroxy-6 beta-methoxy-3 alpha,5-cyclo-5a-cholestane 6, by means of Sharpless asymmetric dihydroxylation of (E)-20(22),24-cholestadiene I is described. Construction of abutasterone-type side chain 4 was carried out by selective mono-dihydroxylation of diene I with (DHQ)(2)AQN, followed by dihydroxylation of the corresponding (24S)-hydroxy-20(22)-cholestene 2 with (DHQD)(2)AQN. In contrast, bis-dihydroxylation of I with either (DHQD)(2)PHAL or (DHQD)(2)AQN preferentially occurs to produce 24-epi-abutasterone-type side chain 6. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.11.001
• 作为产物：
  描述：

  异己基三苯基鏻溴化物 、 (20S)-3α,5-cyclo-20-formyl-6β-methoxy-5α-pregnane 在 potassium 2-methylbutan-2-olate 作用下， 以 苯 为溶剂， 生成 (20E)-6β-methoxy-3α,5-cyclo-5α-cholest-20(22)-ene
  参考文献：
  名称：

  Utility of the Wittig reaction for the construction of side chains of steroids starting from pregnenolone

  摘要：

  DOI：

  10.1021/jo01336a005