5α-androstane-3β,4α,17β-triol | 1038-63-7

• 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: 5α-androstane-3β,4α,17β-triol
• 英文别名: 5α-androstan-3β,4α,17β-triol；androstane-3β,4α,17β-triol；5α-Androstan-3β,4α,117β-triol；(3S,4S,5R,8R,9S,10R,13S,14S,17S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,4,17-triol
• CAS: 1038-63-7
• 化学式: C₁₉H₃₂O₃
• 分子量: 308.461
• InChiKey: UXTGTYSFGWRVQF-ZEMYGLBYSA-N

物化性质

• 沸点：
  436.1±45.0 °C(Predicted)
• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5α-androstane-3β,4α,17β-triol 在 二甲基亚砜 、 三乙胺 、 三氟乙酸酐 作用下， 生成 3-hydroxy-5α-androst-2-ene-4,17-dione
  参考文献：
  名称：

  Improved syntheses of aromatase inhibitors and neuroactive steroids efficient oxidations and reductions at key positions for bioactivity

  摘要：

  DOI：

  10.1016/s0040-4020(98)01138-7
• 作为产物：
  描述：

  雄烯二酮 在 sodium tetrahydroborate 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲醇 、 水 、 苯 为溶剂， 反应 5.0h， 生成 5α-androstane-3β,4α,17β-triol
  参考文献：
  名称：

  Metabolism of 4-hydroxyandrostenedione and 4-hydroxytestosterone: Mass spectrometric identification of urinary metabolites

  摘要：

  4-Hydroxyandrost-4-ene-3,17-dione is a second generation, irreversible aromatase inhibitor and commonly used as anti breast cancer medication for postmenopausal women. 4-Hydroxytestosterone is advertised as anabolic steroid and does not have any therapeutic indication. Both substances are prohibited in sports by the World Anti-Doping Agency, and, due to a considerable increase of structurally related steroids with anabolic effects offered via the internet, the metabolism of two representative candidates was investigated.Excretion studies were conducted with oral applications of 100mg of 4-hydroxyandro-stenedione or 200mg of 4-hydroxytestosterone to healthy male volunteers. Urine samples were analyzed for metabolic products using conventional gas chromatography-mass spectrometry approaches, and the identification of urinary metabolites was based on reference substances, which were synthesized and structurally characterized by nuclear magnetic resonance spectroscopy and high resolution/high accuracy mass spectrometry.Identified phase-I as well as phase-II metabolites were identical for both substances. Regarding phase-I metabolism 4-hydroxyandrostenedione (1) and its reduction products 3 beta-hydroxy-5 alpha-androstane-4,17-dione (2) and 3 alpha-hydroxy-5 beta-androstane-4,17-dione (3) were detected. Further reductive conversion led to all possible isomers of 3 xi,4 xi-dihydroxy,-5 xi-androstan-17-one (4, 6-11) except 3 alpha,4 alpha-dihydroxy-5 beta-androstan-17-one (5).Out of the 17 beta-hydroxylated analogs 4-hydroxytestosterone (18), 3 beta,17 beta-dihydroxy-alpha-androstan-4-one (19),3 alpha,17 beta-dihydroxy-5 beta-androstan-4-one (20), 5 alpha-androstane-3 beta,4 beta,17 beta-triol (21), 5 alpha-androstane-3 alpha,4 beta,17 beta-triol (26) and 5 alpha-androstane-3 alpha,4 alpha,17 beta-triol (28) were identified in the post administration urine specimens. Furthermore 4-hydroxyandrosta-4,6-diene-3,17-dione (29) and 4-hydroxyandrosta-1,4-diene-3,17-dione (30) were determined as oxidation products. Conjugation was diverse and included glucuronidation and sulfatation. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2006.11.018

文献信息

• Regioselective enzymatic acylation of vicinal diols of steroids
  作者：M. Manuel Cruz Silva、Sergio Riva、M. Luisa Sá e Melo

  DOI：10.1016/j.tet.2005.01.104

  日期：2005.3

  Monoacylated derivatives of a complete set of 2,3- and 3,4-vicinal diols of steroids were prepared by regioselective lipase-catalysed transesterification reactions. The enzymes displayed different selectivities towards the vicinal diols depending on the configuration of the hydroxyl groups.

  完整的甾族化合物的2，3-和3，4-邻位二醇的单酰化衍生物是通过区域选择性脂肪酶催化的酯交换反应制备的。取决于羟基的构型，酶对邻二醇具有不同的选择性。
• Synthesis of 4-d1-testosterone and 4-d1-androstenedione.
  作者：TOSHIO NAMBARA、SHIGEO IKEGAWA、HIDEKI ISHIDA

  DOI：10.1248/cpb.24.2486

  日期：——

  In order to clarify the stereochemistry at C-4 in enzymatic saturation of Δ4-3-ketoste-roids synthesis of 4-deuterated testosterone and androst-4-ene-3, 17-dione (XVIII, XIX) has been undertaken. The key intermediate leading to the required substrate, 4α-d1-5α-androstane-3β, 4β, 17β-triol 3, 17-bis (dimethyl-tert-butylsilyl) ether (XVI), was prepared by stereospecific reduction with lithium aluminum deuteride from 3β, 17β-dihydroxy-5α-androstan-4-one disilyl ether (XIII), which was readily obtainable from androst-4-ene-3β, 17β-diol disilyl ether (XI) by hydroboration, followed by oxidation with chromium trioxide-pyridine complex. Dehydration of XVI with phosphorus oxychloride in pyridine provided the Δ4 olefine (XVIIb) which on chromium trioxide oxidation was led to the desired compounds. Reductive dehalogenation of 4-bromotestosterone silyl ether (II) with lithium aluminum deuteride and subsequent oxidation with chromium trioxide-pyridine complex afforded 4-d1-testosterone silyl ether (VII) in which the deuterium incorporation, however, proved to be unsatisfactory.

  为了弄清Δ4-3-酮基类固醇酶饱和合成 4-氚代睾酮和雄甾-4-烯-3，17-二酮（XVIII，XIX）过程中 C-4 的立体化学结构，我们进行了一项研究。所需底物 4α-d1-5α 雄甾烷-3β，4β，17β-三醇 3，17-双（二甲基-叔丁基硅基）醚（XVI）的关键中间体是用氘化铝锂从 3β、17β-二羟基-5α-雄甾烷-4-酮二硅基醚（XIII）的立体还原，然后用三氧化铬-吡啶络合物进行氧化，制备了 3β，17β-二羟基-5α-雄甾烷-4-酮二硅基醚（XVI）。XVI 在吡啶中与氧氯化磷脱水后得到 Δ4 烯烃（XVIIb），再用三氧化铬氧化后得到所需的化合物。用氘化铝锂对 4-溴睾酮硅基醚 (II) 进行还原脱卤反应，然后用三氧化铬-吡啶络合物进行氧化，得到了 4-d1-睾酮硅基醚 (VII)。
• Hanson, James R.; Hitchcock, Peter B.; Liman, Mansur D., Journal of the Chemical Society. Perkin transactions I, 1995, # 17, p. 2183 - 2188
  作者：Hanson, James R.、Hitchcock, Peter B.、Liman, Mansur D.、Naragatnam, Sivajini

  DOI：——

  日期：——
• The Preparation of 5α-Androstane-3β,4α,17β-triol through a Hydroboration Reaction
  作者：Hisao Nakata

  DOI：10.1246/bcsj.38.378

  日期：1965.3