7α,22-dihydroxy-23,24-bisnor-5α-chola-3-one | 301695-48-7

• 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: 7α,22-dihydroxy-23,24-bisnor-5α-chola-3-one
• 英文别名: (5α,7α)-3-ketobisnorcholan-7,22-diol；(20S)-7α,21-dihydroxy-20-methyl-5α-pregn-3-one；(20S)-7α,21-dihydroxy-20-methyl-5α-pregna-3-one；(5S,7R,8R,9S,10S,13R,14S,17R)-7-hydroxy-17-[(2S)-1-hydroxypropan-2-yl]-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
• CAS: 301695-48-7
• 化学式: C₂₂H₃₆O₃
• 分子量: 348.526
• InChiKey: VCUOXSHEOYYSER-YJPOZTGBSA-N

物化性质

• 沸点：
  484.4±20.0 °C(Predicted)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7α,22-dihydroxy-23,24-bisnor-5α-chola-3-one 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 platinum on activated charcoal sodium hypochlorite 、 三甲基氯硅烷 、 硼烷四氢呋喃络合物 、 氢气 、 碳酸氢钠 、 对甲苯磺酸 、 三乙胺 、 sodium bromide 、 sodium t-butanolate 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， -20.0~24.0 ℃ 、344.75 kPa 条件下， 反应 45.75h， 生成 (5S,7R,8R,9S,10S,13R,14S,17R)-7-羟基-17-((2R,5R)-5
  参考文献：
  名称：

  A Short Formal Synthesis of Squalamine from a Microbial Metabolite

  摘要：

  [GRAPHICS]A short formal synthesis of squalamine is described, utilizing the biotransformation product 2, which is available in one step from commercially available 3-keto-23,24-bisnorchol-4-en-22-ol (1), Regioselective C-22 oxidation and C-24 sulfation of the corresponding alcohols in the presence of a free C-7 alcohol make for an efficient preparation of squalamine intermediate 11.

  DOI：

  10.1021/ol0059495
• 作为产物：
  描述：

  3-dioxolane-23,24-bisnorchola-5-en-22-ol 在 ruthenium trichloride 、 platinum on activated charcoal 咪唑 、 盐酸 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 氢气 、 potassium tri-sec-butyl-borohydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 、 乙酸乙酯 为溶剂， 反应 49.0h， 生成 7α,22-dihydroxy-23,24-bisnor-5α-chola-3-one
  参考文献：
  名称：

  Synthesis and antimicrobial activity of squalamine analogue

  摘要：

  Synthesis and antimicrobial activity of squalamine analogue 2 are reported. The synthesis of 2 was accomplished from bisnoralcohol 3. The spermidine moiety was introduced via reductive amination of an appropriately functionalized 3 beta-aminosterol with spermidinyl aldehyde 17 utilizing sodium triacetoxyborohydride as the reducing agent. Compound 2 shows weaker antimicrobial activity than squalamine. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00128-0

文献信息

• Process for the preparation of pregnane derivatives
  申请人：——

  公开号：US20030181742A1

  公开（公告）日：2003-09-25

  A process for preparing pregnane derivatives represented by the formula (V), 1 which comprises the steps of: reacting an alkali (earth) metal with a compound represented by the formula (I) 2 in the presence of ammonia or an amine, to obtain a compound represented by the formula (II); 3 protecting the hydroxy groups of the obtained compound, to obtain a compound represented by the formula (III); 4 protecting the 3-position carbonyl group of the obtained compound, to obtain a compound represented by the formula (IV); 5 and subjecting the obtained compound to solvolysis; and the compound (II).

  一种制备以公式（V）表示的孕烷衍生物的方法，包括以下步骤：在氨或胺的存在下，将以公式（I）表示的化合物与碱金属（碱土金属）反应，得到以公式（II）表示的化合物；保护所得化合物的羟基，得到以公式（III）表示的化合物；保护所得化合物的3位置羰基基团，得到以公式（IV）表示的化合物；将所得化合物进行溶剂解离反应；以及化合物（II）。
• Method for producing 5alpha-pregnane derivative
  申请人：Sugioka Takashi

  公开号：US20070149494A1

  公开（公告）日：2007-06-28

  The present invention relates to a method of producing 5α-pregnane derivatives represented by the formula (II), which is characterized by reacting a pregnane derivative represented by the formula (I) with a metal selected from alkali metals and alkaline earth metals in the presence of a proton donor and an amine and/or ammonia. According to the present invention, a method capable of producing 5α-pregnane derivatives useful as synthetic intermediates for squalamine, in a high yield from easily available raw materials, can be provided: wherein R 1 is a hydroxyl-protecting group, and R 2 , R 11 and R 12 are each independently a hydrogen atom or a hydroxyl-protecting group and R 3 and R 4 are each hydrogen atoms in combination form a bond.

  本发明涉及一种制备式（II）所表示的5α-孕烷衍生物的方法，其特征在于在质子给体和胺和/或氨的存在下，用碱金属和碱土金属中选择的一种金属与式（I）所表示的孕烷衍生物反应。根据本发明，可以提供一种能够从易得的原料中高产得到用作鲨烯合成中间体的5α-孕烷衍生物的方法。其中R1是一个羟基保护基，R2、R11和R12各自独立地是氢原子或羟基保护基，R3和R4在组合时形成一个键，且各自是氢原子。
• Method for Producing 5Alpha-Pregnane Derivative
  申请人：Koyakumaru Kenichi

  公开号：US20070203106A1

  公开（公告）日：2007-08-30

  The present invention relates to a method of producing 5α-pregnane derivatives represented by the formula (III), which is characterized by selectively reducing a carbon-carbon double bond of a 5α-pregnane derivative represented by the formula (II) in a mixture of 5α-pregnane derivatives represented by the formula (I) and the formula (II). According to the present invention, a method capable of producing 5α-pregnane derivatives useful as synthetic intermediates for squalamine, in a high yield from easily available raw materials, can be provided: wherein R 1 , R 2 , R 11 and R 12 are each independently a hydrogen atom or a hydroxyl-protecting group.

  本发明涉及一种生产5α-孕烷衍生物的方法，其表示为公式(III)，其特征在于在公式(I)和公式(II)的5α-孕烷衍生物混合物中，选择性地还原公式(II)中的碳-碳双键。根据本发明，可以提供一种能够从易得到的原料中高产得到用作鲨烷合成中间体的5α-孕烷衍生物的方法。其中，R1、R2、R11和R12各自独立地表示氢原子或羟基保护基。
• METHOD FOR PRODUCING 5ALPHA-PREGNANE DERIVATIVE
  申请人：Kuraray Co., Ltd.

  公开号：EP1743902A1

  公开（公告）日：2007-01-17

  The present invention relates to a method of producing 5α,-pregnane derivatives represented by the formula (II), which is characterized by reacting a pregnane derivative represented by the formula (I) with a metal selected from alkali metals and alkaline earth metals in the presence of a proton donor and an amine and/or ammonia. According to the present invention, a method capable of producing 5α-pregnane derivatives useful as synthetic intermediates for squalamine, in a high yield from easily available raw materials, can be provided: wherein R1 is a hydroxyl-protecting group, and R2, R11 and R12 are each independently a hydrogen atom or a hydroxyl-protecting group and R3 and R4 are each hydrogen atoms in combination form a bond.

  本发明涉及一种生产由式(II)表示的5α-孕烷衍生物的方法，其特征在于由式(I)表示的孕烷衍生物与选自碱金属和碱土金属的金属在质子供体和胺和/或氨的存在下反应。根据本发明，可以提供一种利用容易获得的原料高产率地生产可用作角鲨胺合成中间体的 5α 孕烷衍生物的方法： 其中 R1 是羟基保护基团，R2、R11 和 R12 各自独立地为氢原子或羟基保护基团，R3 和 R4 各自为氢原子，三者结合成键。
• METHOD FOR PRODUCING 5 ALPHA-PREGNANE DERIVATIVE
  申请人：KURARAY CO., LTD.

  公开号：EP1731526A1

  公开（公告）日：2006-12-13

  The present invention relates to a method of producing 5α-pregnane derivatives represented by the formula (III), which is characterized by selectively reducing a carbon-carbon double bond of a 5α-pregnane derivative represented by the formula (II) in a mixture of 5α-pregnane derivatives represented by the formula (I) and the formula (II). According to the present invention, a method capable of producing 5α-pregnane derivatives useful as synthetic intermediates for squalamine, in a high yield from easily available raw materials, can be provided: wherein R1, R2, R11 and R12 are each independently a hydrogen atom or a hydroxyl-protecting group.

  本发明涉及一种生产由式(III)表示的5α-孕甾烷衍生物的方法，其特征在于在由式(I)和式(II)表示的5α-孕甾烷衍生物的混合物中选择性地还原由式(II)表示的5α-孕甾烷衍生物的碳碳双键。根据本发明，可以提供一种利用容易获得的原料高产率生产可用作角鲨胺合成中间体的 5α-孕甾烷衍生物的方法： 其中 R1、R2、R11 和 R12 各自独立地为氢原子或羟基保护基团。