(20R)-20-hydroxy-5β-pregnan-3α-yl acetate | 1900-68-1

• 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: (20R)-20-hydroxy-5β-pregnan-3α-yl acetate
• 英文别名: 3α-acetoxy-5β-pregnan-20β_F-ol；3α,20β-Dihydroxy-5β-pregnan-3-acetat；[(3R,5R,8R,9S,10S,13S,14S,17S)-17-[(1R)-1-hydroxyethyl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 1900-68-1
• 化学式: C₂₃H₃₈O₃
• 分子量: 362.553
• InChiKey: RDRFJIOUMNDZPW-NLQYFYISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (20R)-20-hydroxy-5β-pregnan-3α-yl acetate 在 盐酸 作用下， 生成 5-beta-孕甾烷-3-alpha,20-beta-二醇
  参考文献：
  名称：

  Epimeric 20-Hydroxypregnene Derivatives¹

  摘要：

  DOI：

  10.1021/ja01149a107
• 作为产物：
  描述：

  3α-acetoxy-5β-pregnan-20-one 在 溶剂黄146 、 铂 作用下， 生成 (20R)-20-hydroxy-5β-pregnan-3α-yl acetate
  参考文献：
  名称：

  Epimeric 20-Hydroxypregnene Derivatives¹

  摘要：

  DOI：

  10.1021/ja01149a107

文献信息

• Stereoselectivity of sodium borohydride reduction of saturated steroidal ketones utilizing conditions of Luche reduction
  作者：Eva Šťastná、Ivan Černý、Vladimír Pouzar、Hana Chodounská

  DOI：10.1016/j.steroids.2010.04.010

  日期：2010.10

  A series of keto steroids were reduced with sodium borohydride in the presence of cerium(III) chloride or samarium(III) iodide (Luche reduction). The ratios of axial and equatorial alcohols were determined by HPLC and the results were compared with those obtained by a standard sodium borohydride reduction. The best results were obtained with the 2-keto derivative 1, 7-keto derivatives 5 and 6, and

  在氯化铈（III）或碘化sa（III）的存在下，用硼氢化钠还原一系列酮类固醇（Luche还原）。通过HPLC测定轴向和赤道醇的比例，并将结果与​​通过标准硼氢化钠还原获得的结果进行比较。用2-酮衍生物1、7-酮衍生物5和6以及12-酮衍生物8获得最好的结果，其中铈（III）离子的加入导致轴向/赤道比的倒置。20-酮衍生物11的卢氏还原将（20S）/（20R）醇的混合物中的（20S）-醇的比例从标准的硼氢化钠还原中的5％提高至35％。
• 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.
• Epimeric 20-Hydroxypregnene Derivatives¹
  作者：Richard B. Turner、Dorothy M. Voitle

  DOI：10.1021/ja01149a107

  日期：1951.5