3alpha,7beta-二-O-乙酰基乌苏基脱氧胆酸甲酯 | 60384-30-7

• 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
• 中文名称: 3alpha,7beta-二-O-乙酰基乌苏基脱氧胆酸甲酯
• 英文名称: methyl 3α,7β-diacetoxy-5β-cholan-24-oate
• 英文别名: 3alpha,7beta-Di-O-acetyl Ursodeoxycholic Acid Methyl Ester；methyl (4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-diacetyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 60384-30-7
• 化学式: C₂₉H₄₆O₆
• 分子量: 490.681
• InChiKey: ZKHVKSAMEUAGEN-OSBYRPBFSA-N

物化性质

• 溶解度：
  可溶于丙酮、二氯甲烷、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3alpha,7beta-二-O-乙酰基乌苏基脱氧胆酸甲酯 在 吡啶 、 盐酸 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 methyl (R)-4-((3R,5S,7S,8R,9S,10S,13R,14S,17R)-7-acetoxy-3-(2-hydroxyethoxy)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate
  参考文献：
  名称：

  Novel liver-specific nitric oxide (NO) releasing drugs with bile acid as both NO carrier and targeting ligand

  摘要：

  Novel liver-specific nitric oxide (NO) releasing drugs with bile acid as both the NO carrier and targeting ligand were designed and synthesized by direct nitration of the hydroxyl group in bile acids or the 3-O-hydroxyl alkyl derivatives, with the intact 24-COOH being preserved for hepatocyte specific recognition. Preliminary biological evaluation revealed that oral administrated targeted conjugates could protect mice against acute liver damage induced by acetaminophen or carbon tetrachloride. The nitrate level in the liver significantly increased after oral administration of 1e while nitrate level in the blood did not significantly change. Co-administration of ursodeoxycholic acid (UDCA) significantly antagonized the increase of nitrate in the liver resulted by administration of 1e. (C) 2014 Hui-Fen Wang and Bo-Hua Zhong. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2014.04.001
• 作为产物：
  描述：

  熊去氧胆酸 在 吡啶 、 4-二甲氨基吡啶 、 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 3alpha,7beta-二-O-乙酰基乌苏基脱氧胆酸甲酯
  参考文献：
  名称：

  一种3β-熊去氧胆酸的制备方法

  摘要：

  本发明公开了一种3β‑熊去氧胆酸的合成方法，采用熊去氧胆酸为原料，经过酯化，保护3、7位羟基，选择性脱除3位保护基，氧化3位羟基，然后还原为3β羟基，水解7位、24位保护基得到所述3β‑熊去氧胆酸。本发明合成方法新颖，成本较低，产率高，条件温和，操作简便，环境友好。

  公开号：

  CN109912676B

文献信息

• A highly efficient, stereoselective oxyfunctionalization of unactivated carbons in steroids with dimethyldioxirane†
  作者：Takashi Iida、Takeru Yamaguchi、Ryusei Nakamori、Masahiro Hikosaka、Nariyasu Mano、Junichi Goto、Toshio Nambara

  DOI：10.1039/b104938k

  日期：——

  Oxyfunctionalization of unactivated methine carbon atoms with dimethyldioxirane (DMDO) is studied for various substituted steroids related to the 5β-cholane and 5α-cholestane series. A highly efficient, stereoselective, one-step remote oxidation of specific methine carbons is attained by DMDO oxidation under mild conditions to give a variety of novel mono- and dihydroxylated steroids. The reactivity and site selectivity

  研究了二甲基二环氧乙烷（DMDO）对未活化次甲基碳原子的氧官能化作用 类固醇 与5β-胆烷有关 5α-胆甾烷系列。高效，立体选择的一步式遥控器氧化作用 DMDO可实现特定的次甲基碳 氧化作用 在温和的条件下产生各种新颖的单羟基和二羟基 类固醇。远程氧官能化的反应性和位点选择性受结构和空间环境以及分子中目标次甲基碳原子的电子密度程度的影响。非酶促方法可有效地应用于生物活性物质的有效和短步合成类固醇。
• Osmiumporphyrin-Catalyzed Oxyfunctionalization and Isomerization of Natural (5β)-Bile Acids withtert-Butyl Hydroperoxide
  作者：Shoujiro Ogawa、Keiji Hosoi、Takashi Iida、Yasuo Wakatsuki、Mitsuko Makino、Yasuo Fujimoto、Alan F. Hofmann

  DOI：10.1002/ejoc.200700158

  日期：2007.7

  tert-Butyl hydroperoxide catalyzed by (meso-5,10,15,20-tetramesitylporphyrinate)osmium(II) carbonyl [Os(TMP)CO] was shown to be an efficient, versatile oxyfunctionalization system for the methyl ester peracetate derivatives of a series of common, natural (5β)-bile acids. Hydroxylation at C-5 and C-14, ketonization at C-15 and C-16, and isomerization at C-5 and C-14 in the nucleus were all attained

  由 (meso-5,10,15,20-tetramesitylporphyrinate) 锇 (II) 羰基 [Os(TMP)CO] 催化的叔丁基过氧化氢被证明是用于一系列过乙酸甲酯衍生物的高效、通用的氧官能化系统常见的天然 (5β)-胆汁酸。C-5和C-14的羟基化、C-15和C-16的酮化以及核内C-5和C-14的异构化均一步完成。讨论了控制区域选择性的因素以及这些化合物的形成机制。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Potential Bile Acid Metabolites. 25. Synthesis and Chemical Properties of Stereoisomeric 3.ALPHA.,7.ALPHA.,16- and 3.ALPHA.,7.ALPHA.,15-Trihydroxy-5.BETA.-cholan-24-oic Acids.
  作者：Takashi Iida、Masahiro Hikosaka、Genta Kakiyama、Keisuke Shiraishi、Claudio D. Schteingart、Lee R. Hagey、Huong-Thu Ton-Nu、Alan F. Hofmann、Nariyasu Mano、Junichi Goto、Toshio Nambara

  DOI：10.1248/cpb.50.1327

  日期：——

  Epimeric 3alpha,7alpha,16- and 3alpha,7alpha,15-trihydroxy-5beta-cholan-24-oic acids and some related compounds were synthesized from chenodeoxycholic acid (CDCA) and ursodeoxycholic acid (UDCA), respectively. The key reaction involved one-step remote oxyfunctionalization of unactivated methine carbons at C-17 of CDCA and at C-14 of UDCA as their methyl ester-peracetate derivatives with dimethyldioxirane

  由鹅去氧胆酸（CDCA）和熊去氧胆酸（UDCA）分别合成了差向异构体3alpha，7alpha，16-和3alpha，7alpha，15-三羟基-5beta-cholan-24-oic酸和一些相关化合物。关键反应涉及CDCA的C-17和UDCA的C-14处未活化次甲基碳的一步远程氧官能化，这是它们与二甲基二环氧乙烷（DMDO）形成的过乙酸甲酯衍生物。所得的17α-和14α-羟基衍生物与POCl（3）或浓缩后脱水。H（2）SO（4），相应的Delta（16）-和Delta（14）-不饱和产物通过硼氢化反应进行水合，然后氧化生成3,7,16-和3,7,15-三酮， 分别。用叔丁胺-硼烷络合物将三酮立体选择性还原，得到差向异构体3alpha，7alpha，16-或3alpha，7alpha，仅15-三羟基衍生物。还阐明了在C-24的侧链羧基与胆汁酸中的16α-（或16β-）羟基之间相应的ε-内酯的容易形成。
• Novel derivatives of 3α,7α-dihydroxy-5β-cholan-24-OIC acid (chenodeoxycholic acid) and 3α,7β-dihydroxy-5β-cholan-24-OIC acid (ursodeoxycholic acid)
  作者：David Kritchevsky、Giovanni Poli、Carlo Scolastico、Cesare R. Sirtori

  DOI：10.1016/0039-128x(86)90075-9

  日期：1986.1

  Several 7-acyl cheno- and ursodeoxycholic acids were obtained in good yields starting from the corresponding cheno- and ursodeoxycholic acids, by a diacylation-selective hydrolysis procedure. A superior method for the synthesis of the 7-oleyl derivatives, by a selective acylation procedure, is also presented.