(20S)-5β-pregnan-3α,20-diyl 3-acetate 20-tosylate | 83638-92-0

• 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: (20S)-5β-pregnan-3α,20-diyl 3-acetate 20-tosylate
• 英文别名: 20α-tosyloxy-5β-pregnan-3α-yl acetate；20α_F-(toluene-sulfonyl-(4)-oxy)-3α-acetoxy-5β-pregnane；20α_F-(Toluol-sulfonyl-(4)-oxy)-3α-acetoxy-5β-pregnan
• CAS: 83638-92-0
• 化学式: C₃₀H₄₄O₅S
• 分子量: 516.742
• InChiKey: XANCCOFHPDYKLX-RAYYSDLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.68
• 重原子数：
  36.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (20S)-5β-pregnan-3α,20-diyl 3-acetate 20-tosylate 以 吡啶 为溶剂， 反应 1.0h， 以302 mg的产率得到3α-acetoxy-5β-pregn-17(20)-ene
  参考文献：
  名称：

  Isolation and structural elucidation of the degradation products of pregnanediol disulfate obtained by hot acid hydrolysis (Clinical analysis on steroids. XXI).

  摘要：

  除了主要产品17α-乙基-17β-甲基-18-去氢-5β-雄甾-13-烯-3α-醇（7a）、17α-甲基-D-同雄甾-5β-醇（8）和17α-甲基-17β-氯-D-同雄甾-5β-醇（9），在3 N盐酸回流条件下还获得了孕醇-3,20-二硫酸酯（2）的其他少量降解产物，并通过与合成样品的比较对其结构进行了鉴定。分离得到的类固醇单烯包括5β-孕-3-烯-20α-醇（10a）、5β-孕-2-烯-20α-醇（11a）、5β-孕-20-烯-3α-醇（12a）和5β-孕-17（20）-烯-3α-醇（13a）。以气相色谱法检测到的13a的Z异构体为5β-孕-17（20）-烯-3α-醇（14a），并通过与合成化合物的气相色谱-质谱比较进行了鉴定。分离的类固醇二烯作为混合物包括具有部分D环结构的Δ2和Δ3化合物，对应于7a、12a和13a。虽然它是一个少量产物，5β-孕烷-3α、20β-二醇（16）也被获得，其分离表明在水解过程中形成了C20碳正离子。完整类固醇孕醇（1）的产率仅为获得的总产品的18.4%。

  DOI：

  10.1248/cpb.30.2474
• 作为产物：
  描述：

  孕甾二醇 在 吡啶 、 溶剂黄146 作用下， 生成 (20S)-5β-pregnan-3α,20-diyl 3-acetate 20-tosylate
  参考文献：
  名称：

  Preschoolers' Inhibition in Their Home: Relation to Temperament

  摘要：

  Researchers assessed 58 preschoolers' reactions to an unfamiliar person and unfamiliar objects in their familiar home environment. Children participated in a 30-min procedure designed to elicit behavioral inhibition, including (a) a free-play period with a stranger present, (b) a structured interaction with the stranger, and (c) uncertainty-eliciting tasks, Behaviors representing the child's reactions toward the mother, stranger, and novel objects were coded, Mothers completed a temperament scale. Preschoolers exhibited behaviors indicative of inhibition toward unfamiliar social and nonsocial stimuli; behaviors remained stable across increasingly intrusive episodes. The approach/withdrawal component of temperament was related to behavioral inhibition. Individual differences in mood did not appear to be related to differences in inhibition. Parent reported temperament was related to researcher-observed behaviors.

  DOI：

  10.1080/00221320209598688

文献信息

• Azido analogs of neuroactive steroids
  作者：Lukáš Vidrna、Ivan Černý、Vladimír Pouzar、Jiřina Borovská、Vojtěch Vyklický、Ladislav Vyklický、Hana Chodounská

  DOI：10.1016/j.steroids.2011.04.008

  日期：2011.9

  Analogs of pregnanolone (3 alpha-hydroxy-5 beta-pregnan-20-one), modified in position 17 were prepared. Compounds with 20-keto pregnane side chain replaced completely by azide (17 alpha- and 17 beta-azido-5 beta-androstan-3 alpha-ol), compounds with its part replaced (20-azido-21-nor-5 beta-pregnan-3 alpha-ol), and compounds with keto group only replaced ((20R)- and (20S)-20-azido-5 beta-pregnan-3 alpha-ol) were synthesized using tosylate displacements with sodium azide or Mitsunobu reaction with azoimide. All five azido steroids were converted into corresponding sulfates. Subsequent tests for inhibition of glutamate induced response on NMDA receptors revealed that modification of pregnanolone sulfate side chain with azide did not disturb the activity and some of sulfates tested were more active than parent compound. (C) 2011 Elsevier Inc. All rights reserved.