Δ⁵-3β,24(R),25-trihydroxycholestene-3-acetate | 64727-04-4

• 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: Δ⁵-3β,24(R),25-trihydroxycholestene-3-acetate
• 英文别名: 3β-acetoxy-24,25-dihydroxycholest-5-ene；24(R),25-dihydrocholesteryl-3β-acetate；[(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5,6-dihydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 64727-04-4
• 化学式: C₂₉H₄₈O₄
• 分子量: 460.698
• InChiKey: MIEUIEXNAMROTI-GRTLOYGESA-N

物化性质

• 熔点：
  158-159 °C
• 沸点：
  562.5±30.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Δ⁵-3β,24(R),25-trihydroxycholestene-3-acetate 在 吡啶 、 氢溴酸 、 potassium carbonate 作用下， 以 甲醇 、 氯仿 、 水 、 溶剂黄146 为溶剂， 反应 20.5h， 生成 25-羟基胆甾醇
  参考文献：
  名称：

  摘要：

  The syntheses of (24S)-24,25-epoxycholesterol, (24S)-hydroxycholesterol, and 24-ketocholesterol are described. The compounds belong to oxysterols, which can be considered to be the modulators of cholesterol metabolism. The asymmetric hydroxylation of desmosterol acetate according to Sharpless was used as the key reaction in the stereoselective introduction of functionality in position 24.

  DOI：

  10.1023/a:1015720707433
• 作为产物：
  描述：

  3β-(tetrahydro-2H-pyran-2-yloxy)chol-5-en-24-ol 在 吡啶 、 chromium(VI) oxide 、 盐酸 、 4-二甲氨基吡啶 、 正丁基锂 、 甲基磺酰胺 、 AD-mix-β 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 、 叔丁醇 为溶剂， 反应 77.5h， 生成 Δ⁵-3β,24(R),25-trihydroxycholestene-3-acetate
  参考文献：
  名称：

  摘要：

  The syntheses of (24S)-24,25-epoxycholesterol, (24S)-hydroxycholesterol, and 24-ketocholesterol are described. The compounds belong to oxysterols, which can be considered to be the modulators of cholesterol metabolism. The asymmetric hydroxylation of desmosterol acetate according to Sharpless was used as the key reaction in the stereoselective introduction of functionality in position 24.

  DOI：

  10.1023/a:1015720707433

文献信息

• A highly stereoselective synthesis of C-24 and C-25 oxysterols from desmosterol
  作者：Qian Zhao、Chao Qian、Xin-Zhi Chen

  DOI：10.1016/j.steroids.2016.03.003

  日期：2016.5

  A new highly stereoselective construction of the side chain of the C-24 and C-25 oxysterols has been achieved by using desmosterol acetate as the starting material and an improved Sharpless catalytic asymmetric dihydroxylation with 100% d.e. (diastereomeric excess) as the key step. The result is much better than the usual asymmetric dihydroxylation procedure. t-Butyl nitrite/2,2,6,6-tetramethylpiperidine

  C-24和C-25氧固醇的侧链具有高度立体选择性的新结构，这是通过使用醋酸去甾醇作为起始原料，并以100％的de（非对映异构体过量）作为主要步骤，改进了Sharpless催化不对称二羟基化反应而实现的。结果比通常的不对称二羟基化方法好得多。开发了亚硝酸叔丁酯/ 2,2,6,6-四甲基哌啶N-氧基自由基/ FeCl3催化剂体系，以活化分子氧以进行24-羟基胆固醇的好氧氧化，并以86.2％的收率获得了24-酮胆固醇。以前从未报道过氧化系统。还提出了催化好氧氧化的机理。
• Formal Synthesis of Squalamine from Desmosterol
  作者：Kazuo Okumura、Yutaka Nakamura、Seiji Takeuchi、Isao Kato、Yoshinori Fujimoto、Nobuo Ikekawa

  DOI：10.1248/cpb.51.1177

  日期：——

  The key intermediate to squalamine, (5α,7α,24R)-7,24-dihydroxy-cholestan-3-one, was synthesized from the 3-O-acetyl-24R,25-dihydroxy derivative of desmosterol via 10 steps in 16% overall yield and squalamine was also prepared via two further steps in 7.4% total yield from the desmosterol derivative.

  角鲨胺的关键中间体(5α,7α,24R)-7,24-二羟基胆甾坦-3-酮是由去莫甾醇的3-O-乙酰基-24R,25-二羟基衍生物经10步合成，浓度为16%总产率和角鲨胺还通过另外两个步骤由去莫甾醇衍生物制备，总产率为 7.4%。
• Use of malic acid as a chiral synthon: 24,25-Dihydroxycholecalciferol
  作者：Jeffrey Sterling、Eliot Slovin、Dinorah Barasch

  DOI：10.1016/s0040-4039(00)95394-2

  日期：1987.1
• Efficient, Stereoselective Synthesis of 24(<i>S</i>),25-Epoxycholesterol
  作者：Nicholas C. O. Tomkinson、Timothy M. Willson、Jonathon S. Russel、Thomas A. Spencer

  DOI：10.1021/jo981753v

  日期：1998.12.1

  Efficient, stereoselective syntheses of 24(S),25-epoxycholesterol (1) have been developed starting from cholenic acid (4) or stigmasterol (8), both featuring as the key step Sharpless asymmetric dihydroxylation of desmosterol acetate (2). This work permits preparation of gram quantities of 1 for further evaluation as a natural regulator of cholesterol metabolism, specifically, e.g., as a ligand for the LXR alpha nuclear receptor.