methyl 3α,6α-di(methoxymethyl)hyodeoxycholate | 141069-77-4

• 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: methyl 3α,6α-di(methoxymethyl)hyodeoxycholate
• 英文别名: methyl 3,6-dimethoxymethyl-3α,6α-dihydroxy-5β-cholonate；methyl (4R)-4-[(3R,5R,6S,8S,9S,10R,13R,14S,17R)-3,6-bis(methoxymethoxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 141069-77-4
• 化学式: C₂₉H₅₀O₆
• 分子量: 494.712
• InChiKey: OBYYRQACYWYKDD-SMBJFXTESA-N

物化性质

• 沸点：
  524.5±35.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3α,6α-di(methoxymethyl)hyodeoxycholate 生成 methyl 3α,6α-di(methoxymethyl)-22,23-dehydrohyodeoxycholate
  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：

  二甲醇缩甲醛 、 猪去氧胆酸甲酯 在 phosphorus pentoxide 作用下， 以 氯仿 为溶剂， 反应 8.0h， 以91%的产率得到methyl 3α,6α-di(methoxymethyl)hyodeoxycholate
  参考文献：
  名称：

  A new highly stereoselective synthesis of cerebrosterol, an agonist of the nuclear receptor LXRs

  摘要：

  The title compound, cerebrosterol 1, was synthesized stereoselectively (97% d.e.) in 41% overall yield from methyl hyodeoxycholanate 2 in 10 steps with desmosterol acetate 8 as the key intermediate and the modified Sharpless asymmetric dihydroxylation as the key step. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00812-2

文献信息

• 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
  作者：Wei-Shan Zhou、Liang-Fu Huang

  DOI：10.1016/s0040-4020(01)88509-4

  日期：1992.1

  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.
• A new highly stereoselective synthesis of cerebrosterol, an agonist of the nuclear receptor LXRs
  作者：Xiang-Dong Zhou、Wei-Shan Zhou

  DOI：10.1016/s0040-4020(01)00812-2

  日期：2001.9

  The title compound, cerebrosterol 1, was synthesized stereoselectively (97% d.e.) in 41% overall yield from methyl hyodeoxycholanate 2 in 10 steps with desmosterol acetate 8 as the key intermediate and the modified Sharpless asymmetric dihydroxylation as the key step. (C) 2001 Elsevier Science Ltd. All rights reserved.