(3alpha,5beta,7alpha)-3-[(乙氧羰基)氧基]-7-羟基胆烷-24-酸甲酯 | 61252-49-1

• 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
• 中文名称: (3alpha,5beta,7alpha)-3-[(乙氧羰基)氧基]-7-羟基胆烷-24-酸甲酯
• 英文名称: methyl 3α-(ethoxycarbonyloxy)-7α-(hydroxyl)-5β-cholanoate
• 英文别名: 3α-ethoxycarbonyloxy-7α-hydroxy-5β-cholan-24-oic acid methyl ester；3α-Aethoxycarbonyloxy-7α-hydroxy-5β-cholan-24-saeure-methylester；methyl (4R)-4-[(3R,5R,7R,8R,9S,10S,13R,14S,17R)-3-ethoxycarbonyloxy-7-hydroxy-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: 61252-49-1
• 化学式: C₂₈H₄₆O₆
• 分子量: 478.67
• InChiKey: PVFTVSUIBOGJNP-OLZUBPPLSA-N

物化性质

• 溶解度：
  可溶于丙酮、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3alpha,5beta,7alpha)-3-[(乙氧羰基)氧基]-7-羟基胆烷-24-酸甲酯 在 palladium dihydroxide 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 、 氢气 作用下， 以 甲醇 为溶剂， -78.0 ℃ 、344.73 kPa 条件下， 反应 12.0h， 生成 (R)-4-[(3R,5R,7R,8R,9S,10S,13R,14S,17R)-3-Ethoxycarbonyloxy-10,13-dimethyl-7-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid methyl ester
  参考文献：
  名称：

  非反应性底物的糖基化

  摘要：

  合成这些 de glucosteroide et d'arylglucoside a partir d'ethoxycarbonyloxy-3 hydroxy-7 cholanoate-24 acide et de phenyl tetra-O-benzyl-2,3,4,6 glucopyranosyl sulfoxyde

  DOI：

  10.1021/ja00199a081
• 作为产物：
  描述：

  鹅脱氧胆酸甲酯 、 氯甲酸乙酯 在 吡啶 作用下， 生成 (3alpha,5beta,7alpha)-3-[(乙氧羰基)氧基]-7-羟基胆烷-24-酸甲酯
  参考文献：
  名称：

  Insect Moulting Hormones: The Synthesis of Ecdysone Analogues From a Bile Acid

  摘要：

  以胆汁酸 2-deoxyecdysone 类似物的新的通用合成方法。 酸为起点的 2-脱氧蜕皮激素类似物的一种新的通用合成方法。 进行结构-生物活性研究。

  DOI：

  10.1071/ch9761815

文献信息

• Direct chemical synthesis of β-mannopyranosides and other glycosides via glycosyl triflates
  作者：David Crich、Sanxing Sun

  DOI：10.1016/s0040-4020(98)00426-8

  日期：1998.7

  High yield, highly stereoselective methods for the synthesis of β-mannopyranosides of primary, secondary, and tertiary alcohols are presented. Activation of mannosyl sulfoxides or mannosyl thioglycosides with trifluoromethanesulfonic anhydride or benzenesulfenyl triflate, respectively, leads to the efficient formation of α-mannosyl triflates at −78 °C in dichloromethane, in the presence of 2,6-di-

  提出了伯醇，仲醇和叔醇的β-甘露吡喃糖苷合成的高产率，高立体选择性的方法。在存在2,6-二叔丁基-4-甲基吡啶。这些三氟甲磺酸酯反应，然后小号Ñ 2样与醇得到的β型甘露糖苷。为了实现高选择性，需要使用4,6- O-亚苄基保护的甘露糖，以及使用O -2和O上的非参与性保护基团-3个捐助者。进一步证明，当耐受武装和解除武装的保护基团时，硫代糖苷/苯磺酰基三氟甲磺酸酯的活化适用于葡糖苷系列。
• Direct Formation of β-Mannopyranosides and Other Hindered Glycosides from Thioglycosides
  作者：David Crich、Sanxing Sun

  DOI：10.1021/ja9734814

  日期：1998.1.1
• Chemical synthesis of 3β-sulfooxy-7β-hydroxy-24-nor-5-cholenoic acid: An internal standard for mass spectrometric analysis of the abnormal Δ5-bile acids occurring in Niemann-Pick disease
  作者：Genta Kakiyama、Akina Muto、Miki Shimada、Nariyasu Mano、Junichi Goto、Alan F. Hofmann、Takashi Iida

  DOI：10.1016/j.steroids.2009.04.007

  日期：2009.9

  In Niemann-Pick disease, type C1, increased amounts of 3 beta,7 beta-dihydroxy-5-cholenoic acid are reported to be present in urinary bile acids. The compound occurs as a tri-conjugate, sulfated at C-3, N-acetylglucosamidated at C-7, and N-acylamidated with taurine or glycine at C-24. For sensitive LC-MS/MS analysis of this bile acid, a suitable internal standard is needed. We report here the synthesis of a satisfactory internal standard, 3 beta-sulfooxy-7 beta-hydroxy-24-nor-5-cholenoic acid (as the disodium salt). The key reactions involved were (1) the so-called "second order" Beckmann rearrangement (one-carbon degradation at C-24) of hyodeoxycholic acid (HDCA) 3,6-diformate with sodium nitrite in a mixture of trifluoroacetic anhydride and trifluoroacetic acid, (2) simultaneous inversion at C-3 and elimination at C-6 of the ditosylate derivatives of the resulting 3 alpha,6 alpha-dihydroxy-24-nor-5 beta-cholanoic acid with potassium acetate in aqueous N,N-dimethylformamide, and (3) regioselective sulfation at C-3 of an intermediary 3 beta,7 beta-dihydroxy-24-nor-Delta(5) derivative using sulfur trioxide-trimethylamine complex. Overall yield of the desired compound was 1.8% in 12 steps from HDCA. (C) 2009 Elsevier Inc. All rights reserved.
• Synthesis and comparative spectroscopic analysis of two chenodeoxycholic acid (CDCA) derivatives with closely related 7α-ester moieties
  作者：Xinyan Bai、Charles Barnes、Jerry Ray Dias

  DOI：10.1016/j.tetlet.2008.11.052

  日期：2009.2

  3 alpha-Hydroxyl-7 alpha-(4-pentenoyloxy)-5 beta-cholanoic acid (5) has been synthesized in four step reactions starting from CDCA. The serendipitous synthesis of methyl 3 alpha-(allyloxycarbonyloxy)-7 alpha-(allyloxycarbonyloxy)-5 beta-cholanoate (7) has led us to compare the spectroscopic difference of the 7 alpha-(allyloxycarbonyloxy)group versus the 7 alpha-(4-pentenoyloxy) group. The molecular Structures of these compounds were confirmed by X-ray Crystallography. Methyl 3 alpha-(ethoxycarbonyloxy)-7 alpha-(allyloxycarbonyloxy)-5 beta-cholanoate was obtained by a method, which may prove useful in the synthesis of C-14-labeled derivatives for metabolic studies. (c) 2008 Elsevier Ltd. All rights reserved.
• Dehydration of Bile Acids and their Derivatives. VII. Isomerization of Methyl 3α-Hydroxy-<i>Δ</i>⁷-cholenate to Methyl 3α-Hydroxy-<i>Δ</i>¹⁴-cholenate
  作者：Ryuzaburo Osawa、Kazumi Yamasaki

  DOI：10.1246/bcsj.32.1302

  日期：1959.12