17α-methyl-2β,3α,17β-trihydroxy-5α-androstane | 1375064-29-1

• 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: 17α-methyl-2β,3α,17β-trihydroxy-5α-androstane
• 英文别名: 17alpha-Methyl-2beta,3alpha,17beta-trihydroxy-5alpha-androstane；(2S,3S,5S,8R,9S,10S,13S,14S,17S)-10,13,17-trimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthrene-2,3,17-triol
• CAS: 1375064-29-1
• 化学式: C₂₀H₃₄O₃
• 分子量: 322.488
• InChiKey: BUTNDYMNFYGFDE-PEACWCRISA-N

物化性质

• 沸点：
  438.5±35.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 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

• 作为产物：
  描述：

  17β-hydroxy-17α-methyl-2,3α-spirooxirane-5α-androstane 在 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以75%的产率得到17α-methyl-2β,3α,17β-trihydroxy-5α-androstane
  参考文献：
  名称：

  Characterization of desoxymethyltestosterone main urinary metabolite produced from cultures of human fresh hepatocytes

  摘要：

  Desoxymethyltestosterone (DMT; 17 beta-hydroxy-17 alpha-methyl-5 alpha-androst-2-ene) is a designer steroid present in hormonal supplements distributed illegally as such or in combination with other steroids, for self-administration. It figures on the list of substances prohibited in sports and its detection in athlete's urine samples is based upon the presence of the parent compound or the main urinary metabolite, which has not been characterized yet. Following its isolation from cultures of human fresh hepatocytes and S9 fractions of liver homogenates, we were able to identify this metabolite as being 17 alpha-methyl-2 beta,3 alpha,17 beta-trihydroxy-5 alpha-androstane. Other minor metabolites were also characterized. The production, isolation, NMR, mass spectral analyses and chemical synthesis are presented. (c) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.02.008

文献信息

• METHODS AND COMPOUNDS FOR PREPARING 3ALPHA-OXYGEN SUBSTITUTED STEROIDS
  申请人：Ge Yu

  公开号：US20120214987A1

  公开（公告）日：2012-08-23

  The invention relates to processes for preparing 3α-O-linked steroids including 3α-O-linked-androst-5-ene steroids and 3α-O-linked-5a-androstane steroids. In one process a 3α,4α-epoxy androst-5-en-17-one is predominately reduced at the epoxy moiety wherein reduction of the 3α,4α epoxy functional group occurs preferentially at position C4 with retention of configuration at position C3 to provide a 3α-O-linked-androst-5-ene steroid. In another process, conditions are provided for inversion of configuration of a 3β-hydroxy-androst-5-ene steroid by the Mitsunobu reaction to provide a 3α-O-linked-androst-5-ene steroid with reduced amounts of 3α,5α-cycloandrostane side-product impurities.

  该发明涉及制备3α-O-连接类固醇的过程，包括3α-O-连接-雄烯类固醇和3α-O-连接-5α-雄烷类固醇。在一个过程中，3α,4α-环氧基雄-5-烯-17-酮主要在环氧基团处还原，其中3α,4α-环氧官能团的还原优先发生在C4位置，并保留C3位置的构型，以提供3α-O-连接-雄烯类固醇。在另一个过程中，通过Mitsunobu反应提供条件，使3β-羟基雄-5-烯类固醇的构型发生倒置，以提供含有减少量3α,5α-环雄烷副产物杂质的3α-O-连接-雄烯类固醇。
• [EN] METHODS AND COMPOUNDS FOR PREPARING 3ALPHA-OXYGEN SUBSTITUTED STEROIDS<br/>[FR] PROCÉDÉS ET COMPOSÉS UTILISÉS POUR PRÉPARER DES STÉROÏDES 3 ALPHA-OXYGÈNE SUBSTITUÉS
  申请人：HARBOR BIOSCIENCES INC

  公开号：WO2012083090A2

  公开（公告）日：2012-06-21

  The invention relates to processes for preparing 3α-O-linked steroids including 3α-O-linked-androst-5-ene steroids and 3α-O-linked-5α-androstane steroids. In one process a 3α,4α-epoxy androst-5-en-17-one is predominately reduced at the epoxy moiety wherein reduction of the 3α,4α epoxy functional group occurs preferentially at position C4 with retention of configuration at position C3 to provide a 3α-O-linked-androst-5-ene steroid. In another process, conditions are provided for inversion of configuration of a 3β-hydroxy-androst-5-ene steroid by the Mitsunobu reaction to provide a 3α-O-linked-androst-5-ene steroid with reduced amounts of 3α,5α-cycloandrostane side-product impurities.