3α-hydroxy-5α-androstan-17β-yl β-D-glucopyranosiduronic acid | 95237-44-8

• 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: 3α-hydroxy-5α-androstan-17β-yl β-D-glucopyranosiduronic acid
• 英文别名: 5α-androstane-3α,17β-diol-17-O-glucuronide；5α-androstane-3α-ol-17β-O-glucuronide；androstanediol 17-glucuronide；Androstane-3,17-diol Glucuronide；Androstanediol-17g；(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[[(3R,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]oxy]oxane-2-carboxylic acid
• CAS: 95237-44-8
• 化学式: C₂₅H₄₀O₈
• 分子量: 468.588
• InChiKey: ZJYZOWMDMWQJIV-WWLGJQRMSA-N

物化性质

• 沸点：
  656.3±55.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  组胺 、 3α-hydroxy-5α-androstan-17β-yl β-D-glucopyranosiduronic acid 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 312.0h， 以34%的产率得到3α-hydroxy-5α-androstan-17β-yl N-(4-imidazolyl)ethyl-β-D-glucopyranosiduronamide
  参考文献：
  名称：

  Synthesis of 5α-androstane-3α,17β-diol 17-O-glucuronide histaminyl conjugate for immunoassays

  摘要：

  Simple method of preparation of 5 alpha-androstane-3 alpha,17 beta-diol 17-O-glucuronide N-histaminyl amide was developed for the construction of immunoanalytical kit. Improved method of glucuronide derivative synthesis was used, followed by hydroxybenzotriazole-dicyclohexylcarbodiimide coupling with histamine. (C) 2016 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2016.02.011
• 作为产物：
  描述：

  乙酸雄甾酮 在 sodium tetrahydroborate 、 silver carbonate 、 lithium hydroxide 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 、 乙酸乙酯 、 苯 为溶剂， 反应 144.0h， 生成 3α-hydroxy-5α-androstan-17β-yl β-D-glucopyranosiduronic acid
  参考文献：
  名称：

  Synthesis of 5α-androstane-3α,17β-diol 17-O-glucuronide histaminyl conjugate for immunoassays

  摘要：

  Simple method of preparation of 5 alpha-androstane-3 alpha,17 beta-diol 17-O-glucuronide N-histaminyl amide was developed for the construction of immunoanalytical kit. Improved method of glucuronide derivative synthesis was used, followed by hydroxybenzotriazole-dicyclohexylcarbodiimide coupling with histamine. (C) 2016 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2016.02.011

文献信息

• Mass spectrometry of steroid glucuronide conjugates. II-Electron impact fragmentation of 3-keto-4-en- and 3-keto-5α-steroid-17-<i>O</i>-β glucuronides and 5α-steroid-3α,17β-diol 3- and 17-glucuronides
  作者：Mario Thevis、Georg Opfermann、Hans Schmickler、Wilhelm Schänzer

  DOI：10.1002/jms.203

  日期：2001.9

  means of the Koenigs-Knorr reaction. Selective 3- or 17-O-conjugation of bis-hydroxylated steroids was performed either by glucuronidation of the corresponding steroid ketole and subsequent reduction of the keto group or via a four-step synthesis starting from a mono-hydroxylated steroid including (a) protection of the hydroxy group, (b) reduction of the keto group, (c) conjugation reaction and (d) removal

  16,16,17-d（3）-睾丸激素，表睾酮，nandrolone（19-nortestosterone），16,16,17-d（3）-nortestosterone，甲基睾丸激素，metenolone，mesterolone，5alpha-androstane- 3alpha，17beta-二醇，2,2,3,4,4-d（5）-5alpha-雄甾烷-3alpha，17beta-二醇，19-nor-5alpha-androstane-3alpha，17beta-二醇，2,2,4通过Koenigs-Knorr反应合成了1-4-d（4）-19-nor-5α-雄甾烷-3α，17β-二醇和1α-甲基-5α-雄烷-3α/β，17β-二醇。选择性3-或双 - 羟基化类固醇17-O-缀合由相应的类固醇ketole和通过四步合成从单羟基化的类固醇包括（a）保护起始酮基或随后的还原的葡萄糖醛酸化任一执行（b）
• Enzyme-assisted synthesis and structure characterization of glucuronide conjugates of eleven anabolic steroid metabolites
  作者：Laura Hintikka、Tiia Kuuranne、Olli Aitio、Mario Thevis、Wilhelm Schänzer、Risto Kostiainen

  DOI：10.1016/j.steroids.2007.10.008

  日期：2008.3

  Enzyme-assisted in vitro synthesis of eleven glucuronide-conjugated anabolic androgenic steroid (AAS) metabolites was performed using biphenyl-induced rat liver microsomal enzymes. The substrates within the study were the main compounds and metabolites detected in human urine after dosing of, e.g. metandienone, metenolone, methyltestosterone, nandrolone, and testosterone. Yields of glucuronidation reactions were 13-28% for most compounds, but significantly higher (77-78%) for the substrates with 4-ene-3-one double bond system of the steroid A-ring. Characterization of glucuronide-conjugated AAS structures was based on nuclear magnetic resonance spectroscopy (H-1 NMR) and on liquid chromatographic-mass spectrometric (LC-MS) and tandem mass spectrometric (LC-MS/MS) analyses in positive and negative ion mode electrospray ionization (ESI). Only minor differences were observed in optimal synthesis conditions between various substrates, which offer a potential to apply this in vitro assay as a default method for glucuronidation of new AAS substrates. The method allowed for a rapid production pathway of stereochemically pure AAS glucuronides in milligram amount, such as needed, e.g. in the development of analytical methods in forensic or pharmaceutical sciences, as well as in doping control. (C) 2007 Elsevier Inc. All rights reserved.
• Synthesis of a precursor for the preparation of 9α, 11α-tritiated 5α-androstane-3α,17β-diol 17-glucuronide
  作者：P.Narasimha Rao、K.M. Damodaran

  DOI：10.1016/0039-128x(84)90052-7

  日期：1984.3

  Starting from 11 beta-hydroxytestosterone, we achieved the synthesis of a strategic precursor, C-9 (11) unsaturated 5 alpha-androstane-3 alpha, 17 beta-diol 17-glucuronide (9a), for the preparation of 9 alpha,11 alpha-tritiated 5 alpha-androstane-3 alpha, 17 beta-diol 17-glucuronide. We optimized the reaction conditions for catalytic reduction employing hydrogen and subsequent base hydrolysis followed by purification on Amberlite XAD-2 resin to obtain the saturated 5 alpha-androstane-3 alpha, 17 beta-diol 17-glucuronide.
• Synthesis of 5α-androstane-3α,17β-diol 17-O-glucuronide histaminyl conjugate for immunoassays
  作者：Petr Vinš、Ivan Černý、Petra Mikšátková、Pavel Drašar

  DOI：10.1016/j.steroids.2016.02.011

  日期：2016.5

  Simple method of preparation of 5 alpha-androstane-3 alpha,17 beta-diol 17-O-glucuronide N-histaminyl amide was developed for the construction of immunoanalytical kit. Improved method of glucuronide derivative synthesis was used, followed by hydroxybenzotriazole-dicyclohexylcarbodiimide coupling with histamine. (C) 2016 Elsevier Inc. All rights reserved.