(20E)-6β-methoxy-3α,5-cyclo-5α-cholesta-20(22),24-diene | 874291-81-3

• 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-cholesta-20(22),24-diene
• 英文别名: (1S,2R,5R,7R,8R,10S,11S,14R,15S)-8-methoxy-2,15-dimethyl-14-[(2E)-6-methylhepta-2,5-dien-2-yl]pentacyclo[8.7.0.02,7.05,7.011,15]heptadecane
• CAS: 874291-81-3
• 化学式: C₂₈H₄₄O
• 分子量: 396.657
• InChiKey: KGGMZGUPTVFRCT-OCOASHRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (20E)-6β-methoxy-3α,5-cyclo-5α-cholesta-20(22),24-diene 在 四氧化锇 、 (DHQ)2AQN 、 hydroquinidine anthraquinone-1,4-diyl diether 作用下， 以 叔丁醇 为溶剂， 生成 (20R,22R,24S)-20,22,24,25-tetrahydroxy-6β-methoxy-3α,5-cyclo-5α-cholestane
  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：

  (4-methylpent-3-en-1-yl)triphenylphosphonium bromide 、 (20S)-3α,5-cyclo-20-formyl-6β-methoxy-5α-pregnane 在 sodium hydride 作用下， 以 二甲基亚砜 、 苯 为溶剂， 反应 1.0h， 以86%的产率得到(20E)-6β-methoxy-3α,5-cyclo-5α-cholesta-20(22),24-diene
  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

文献信息

• Studies on the construction of abutasterone-type and 24-epi-abutasterone-type side chains employing asymmetric dihydroxylation of (E)-20(22),24-cholestadiene
  作者：Masayoshi Tsubuki、Kazuo Iwabuchi、Toshio Honda

  DOI：10.1016/j.tetasy.2005.11.001

  日期：2005.11

  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.