3β,5α-dihydroxycholestan-4β-yl acetate | 96376-52-2

• 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: 3β,5α-dihydroxycholestan-4β-yl acetate
• 英文别名: 3β,5α-Dihydrocholestan-4β-yl acetate；4β-acetoxy-5α-cholestane-3β,5-diol；4β-Acetoxy-5α-cholestan-3β,5-diol；4β-Acetoxy-3β,5-dihydroxy-5α-cholestan；4β-Acetoxy-5α-cholestandiol-(3β,5)；[(3S,4S,5S,8S,9S,10R,13R,14S,17R)-3,5-dihydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-4-yl] acetate
• CAS: 96376-52-2
• 化学式: C₂₉H₅₀O₄
• 分子量: 462.714
• InChiKey: RDLMXVPGWYDYTM-DDQKCFFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.97
• 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：

  3β,5α-dihydroxycholestan-4β-yl acetate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 cholestane-3β,4β,5α-triol
  参考文献：
  名称：

  Julia,S.; Lavaux,J.-P., Bulletin de la Societe Chimique de France, 1963, p. 1238 - 1241

  摘要：

  DOI：
• 作为产物：
  描述：

  (4,5)α-epoxy-5α-cholestan-3β-ol 在 高氯酸 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 3β,5α-dihydroxycholestan-4β-yl acetate
  参考文献：
  名称：

  Isolation and structure elucidation of seven new polyhydroxylated sulfated sterols from the ophiuroid Ophiolepis superba

  摘要：

  DOI：

  10.1021/jo00262a049

文献信息

• The synthesis of A- and B-ring fluorinated analogues of cholesterol
  作者：Michael G. Thomas、Colin J. Suckling、Andrew R. Pitt、Keith E. Suckling

  DOI：10.1039/a904826j

  日期：——

  The synthesis of a number of mono- and difluorinated steroids with the potential to act as probes of the metabolism of cholesterol is described. 2α-Fluorocholestan-3-one 7, 4-fluorocholest-5-en-3-one 11 and 6-fluorocholest-4-en-3-one 12 were synthesised from the appropriate silyl enol ethers using 1-fluoropyridinium triflate, and subsequently reduced to the corresponding alcohols, 8, 13 and 14 respectively

  描述了许多具有作为胆固醇代谢探针的潜力的单氟化和二氟化的类固醇的合成。使用三氟甲磺酸1-氟吡啶鎓从合适的甲硅烷基烯醇醚合成2α-氟胆甾烷-3-酮7、4-氟胆甾-5-烯-3-酮11和6-氟胆甾-4-烯-3-酮12还原成相应的醇，分别为8、13和14。使用类似的方法从单氟类固醇7开始合成2,2-二氟胆甾烷-3-醇16。为了合成4,4-二氟胆甾聚糖-3β-ol26，通过酸生成3β-乙酰氧基胆甾烷-4-酮25催化4,5-epoxycholestan-3-one 20的重排并用DAST处理。最后，使用氯二氟乙酸合成了胆固醇28的二氟环丙基类似物。
• Reactions of epoxides—II
  作者：J.M. Coxon、M.P. Hartshorn、D.N. Kirk

  DOI：10.1016/s0040-4020(01)90833-6

  日期：1964.1

  3β-Acetoxy-4α,5-epoxy-5α-cholestane is rearranged by boron trifluoride to give 3β-acetoxy-5β-cholestan-4-one (IV). Under similar reaction conditions the 3α-acetox-4β,5β-epoxide gives a stable 3α,5α-bridged ionic complex, and the 3β-acetoxy-4β,5β epoxide gives the fluorohydrin (X).

  用三氟化硼将3β-乙酰氧基-4α，5-环氧-5α-胆甾烷重排，得到3β-乙酰氧基-5β-胆甾烷-4-酮（IV）。在相似的反应条件下，3α-乙酰氧基-4β，5β-环氧化物生成稳定的3α，5α-桥联离子络合物，3β-乙酰氧基-4β，5β环氧化物生成氟代醇（X）。
• Selective Cytotoxicity of Oxysterols through Structural Modulation on Rings A and B. Synthesis, in Vitro Evaluation, and SAR
  作者：João F. S. Carvalho、M. Manuel Cruz Silva、João N. Moreira、Sérgio Simões、M. Luisa Sá e Melo

  DOI：10.1021/jm200803d

  日期：2011.9.22

  Chemically diverse oxysterols were prepared and evaluated for cytotoxicity, aiming to push forward potency and selectivity. They were tested against seven cancer (HT-29, HepG2, A549, PC3, LAMA-84, MCF-7, and SH-SYSY) and two noncancerous cell lines (ARPE-19 and BJ). The influence of the oxidation pattern on rings A and B was studied. Oxygen functionalities on ring B, such as oxo, oxime, acetamide, acetate, and alkoxy, were evaluated. Most oxysterols were cytotoxic in the low micromolar range, with emphasis to the tetrols 14 and 34, the 6 beta methoxy and acetoxy derivatives 21 and 45, and the oxime 28. In general, the oxysterols were more toxic to cancer cells and a set of compounds (9, 14, 21, 28, 45) with very high selectivity was identified. The cytotoxicity of 3 beta-acetates was lower than that of the parent alcohols, although incubation for a longer period rendered them equally cytotoxic, pointing them as potential prodrugs of oxysterols.
• 788. Steroidal αβ-epoxy-ketones. Part I. Rearrangement of 4α,5-epoxy-5α-cholestan-3-one and its 4β,5β-isomer by means of the boron trifluoride–ether complex
  作者：D. J. Collins

  DOI：10.1039/jr9590003919

  日期：——
• Isolation and structure elucidation of seven new polyhydroxylated sulfated sterols from the ophiuroid Ophiolepis superba
  作者：M. Valeria D'Auria、Raffaele Riccio、Eugenio Uriarte、Luigi Minale、Junichi Tanaka、Tatsuo Higa

  DOI：10.1021/jo00262a049

  日期：1989.1