(22R,23R)-22,23-isopropylidenedioxy-24-methyl-5β-26,27-bisnorcholestane-3,6-diol | 138616-96-3

• 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: (22R,23R)-22,23-isopropylidenedioxy-24-methyl-5β-26,27-bisnorcholestane-3,6-diol
• 英文别名: (22R,23R)-22,23-isopropylidenedioxy-24,24-dimethyl-5β-cholane-3α,6α-diol；(3R,5R,6S,8S,9S,10R,13S,14S,17R)-17-[(1S)-1-[(4R,5R)-2,2-dimethyl-5-propan-2-yl-1,3-dioxolan-4-yl]ethyl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,6-diol
• CAS: 138616-96-3
• 化学式: C₂₉H₅₀O₄
• 分子量: 462.714
• InChiKey: MABWXTXSAWKAEZ-AYLITXBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (22R,23R)-22,23-isopropylidenedioxy-24-methyl-5β-26,27-bisnorcholestane-3,6-diol 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (22R,23R)-22,23-isopropylidenedioxy-24-methyl-5α-cholestane-3,6-dione
  参考文献：
  名称：

  Studies on steroidal plant-growth regulator 25. Concise stereoselective construction of sidechain of brassinosteroid from the intact sidechain of hyodeoxycholic acid: formal syntheses of brassinolide, 25-methylbrassinolide, 26, 27-bisnorbrassinolide and their related compounds

  摘要：

  A concise stereoselective construction of sidechain of brassinolide (1), 25-methylbrassinolide (3) and 26,27-bisnorbrassinolide (4), which involves beta-alkylative 1,3- carbonyl transposition of the alpha,beta-unsaturated ketones 11 and 34 and alpha, beta-unsaturated methyl ester 26, using the intact sidechain of hyodeoxycholic acid (2) as starting material, is described. The formal syntheses of 1, 3 and 4 were accomplished. In the mean time, 25-methylcastasterone (21), 26,27-bisnortyphasterol (6) and the new 25-methyltyphasterol (5) were also syntehesized.

  DOI：

  10.1016/s0040-4020(01)88509-4
• 作为产物：
  描述：

  在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 (22R,23R)-22,23-isopropylidenedioxy-24-methyl-5β-26,27-bisnorcholestane-3,6-diol
  参考文献：
  名称：

  Studies on steroidal plant-growth regulator 25. Concise stereoselective construction of sidechain of brassinosteroid from the intact sidechain of hyodeoxycholic acid: formal syntheses of brassinolide, 25-methylbrassinolide, 26, 27-bisnorbrassinolide and their related compounds

  摘要：

  A concise stereoselective construction of sidechain of brassinolide (1), 25-methylbrassinolide (3) and 26,27-bisnorbrassinolide (4), which involves beta-alkylative 1,3- carbonyl transposition of the alpha,beta-unsaturated ketones 11 and 34 and alpha, beta-unsaturated methyl ester 26, using the intact sidechain of hyodeoxycholic acid (2) as starting material, is described. The formal syntheses of 1, 3 and 4 were accomplished. In the mean time, 25-methylcastasterone (21), 26,27-bisnortyphasterol (6) and the new 25-methyltyphasterol (5) were also syntehesized.

  DOI：

  10.1016/s0040-4020(01)88509-4

文献信息

• Studies on steroidal plant-growth regulator 21. A stereoselective construction of brassinosteroid side chain: a new practical synthesis of brassinolide and its analogues
  作者：Wei-Shan Zhou、Liang-Fu Huang、Li-Qiang Sun、Xin-Fu Pan

  DOI：10.1016/s0040-4039(00)93592-5

  日期：1991.11

  The high stereoselectivity in osmium tetroxide catalyzed asymmetric dihydroxylation of Δ22(23)-methyl hyodeoxycholate has been achieved, and the utilizing of (22R,23S)-22,23-dihydroxy methyl hyodeoxycholate as starting material for syntheses of brassinolide and its analogues is described.

  在四氧化催化的Δ22 （23）-甲基去氧胆酸酯的不对称二羟基化反应中实现了高立体选择性，并且利用（22R，23S）-22,23-二羟基甲基去氧胆酸酯作为合成油菜素内酯及其类似物的原料是描述。
• Zhou, Wei-Shan; Huang, Liang-Fu; Sun, Li-Qiang, Journal of the Chemical Society. Perkin transactions I, 1992, # 15, p. 2039 - 2044
  作者：Zhou, Wei-Shan、Huang, Liang-Fu、Sun, Li-Qiang、Pan, Xin-Fu

  DOI：——

  日期：——