3α-ethoxycarbonyloxy-7α,12α-dihydroxy-5β-cholan-24-oic acid methyl ester | 21059-36-9

• 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: 3α-ethoxycarbonyloxy-7α,12α-dihydroxy-5β-cholan-24-oic acid methyl ester
• 英文别名: 3α-Aethoxycarbonyloxy-7α,12α-dihydroxy-5β-cholan-24-saeure-methylester；7α.12α-Dihydroxy-3α-aethoxycarbonyloxy-5β-cholansaeure-(24)-methylester；Cholic acid, methyl ester, 3-(ethyl carbonate)；methyl (4R)-4-[(3R,5R,7R,8R,9S,10S,12S,13R,14S,17R)-3-ethoxycarbonyloxy-7,12-dihydroxy-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: 21059-36-9
• 化学式: C₂₈H₄₆O₇
• 分子量: 494.669
• InChiKey: KIRFLCKWEBLZMD-XBOGZSQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3α-ethoxycarbonyloxy-7α,12α-dihydroxy-5β-cholan-24-oic acid methyl ester 在 jones' reagent 作用下， 以 丙酮 为溶剂， 反应 0.17h， 以80.6%的产率得到3alpha-[(乙氧羰基)氧基]-7,12-二氧代-5beta-胆烷-24-酸甲酯
  参考文献：
  名称：

  Cyclocholates with 12-Oxo and 7,12-Oxo Groups

  摘要：

  Syntheses of bile acid cyclooligomers with 12- and 7,12-oxo groups (6a-d, 7a-c, 8a-b) by the Yamaguchi method are described. Cyclotrimerization is the principal reaction route for these cholic acid systems. Conversion of 7- and 12-hydroxy groups in cholic acid (1a-b) to oxo groups (4a-c, 5a-c), followed by macrocyclization (6a-d, 7a-c, 8a-b) and selective reduction of the oxo groups back to hydroxy ones without cleaving the 24-carboxylic ester Linkages (11) constitutes a new strategy in the synthesis of cyclocholates having unprotected hydroxy groups.

  DOI：

  10.1002/(sici)1099-0690(199804)1998:4<719::aid-ejoc719>3.0.co;2-f
• 作为产物：
  描述：

  胆酸 在 吡啶 、 盐酸 作用下， 生成 3α-ethoxycarbonyloxy-7α,12α-dihydroxy-5β-cholan-24-oic acid methyl ester
  参考文献：
  名称：

  Selective Oxidation with N-Bromosuccinimide. II. Cholestane-3β,5α,6β-triol

  摘要：

  DOI：

  10.1021/ja01180a016

文献信息

• Synthesis of mosesin-4, a naturally occurring steroid saponin with shark repellent activity, and its analog 7-β-galactosyl ethyl cholate
  作者：Dario Gargiulo、Timothy A. Blizzard、Koji Nakanishi

  DOI：10.1016/s0040-4020(01)89488-6

  日期：——

  The first synthesis of mosesin-4 (13), a naturally occurring steroid saponin with shark repellent activity, and its analog 19, isdescribed. They both possess a free galactose residue attached axially at the 7α position of the steroidal aglycon. Methyl cholate 3-cathylate (2) was used as a model for exploring various several methods to glycosidate the severely hindered 7α-position. Best results were

  描述了mosesin-4（13）的首次合成，mosesin-4（13）是一种天然的具有鲨鱼驱避活性的甾体皂苷，及其类似物是19。它们都具有轴向连接在甾体糖苷配基的7α位置的游离半乳糖残基。胆酸3-邻苯二甲酸甲酯（2）被用作探索多种方法糖基化严重受阻的7α-位的模型。使用三氟甲磺酸三甲基甲硅烷基酯作为促进剂，在20°C的1,2-二氯乙烷中，用β-半乳糖五乙酸酯（3a）可获得14个小时的最佳结果。
• Synthesis of a Scaffold for the Creation of Non-Peptide Libraries
  作者：Alexander Kasal、Ladislav Kohout、Michal Lebl

  DOI：10.1135/cccc19952147

  日期：——

  5β-Cholanic acid derivative XVII was prepared as a skeleton for the creation of non-peptide libraries. In positions 3, 7 and 12, different functional groups were designed in order to provide for the attachment of various building blocks linked to them.

  5β-胆酸衍生物XVII被制备为非肽库创建的骨架。在3、7和12位置设计了不同的功能基团，以便连接各种构建块。
• Glycosylation of unreactive substrates
  作者：Daniel Kahne、Suzanne Walker、Yuan Cheng、Donna Van Engen

  DOI：10.1021/ja00199a081

  日期：1989.8

  Synthese 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

  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
• Cathylation (Carbethoxylation) of Steroid Alcohols
  作者：Louis F. Fieser、Josef E. Herz、Murle W. Klohs、Miguel A. Romero、Torlief Utne

  DOI：10.1021/ja01133a027

  日期：1952.7
• Borsche, Chemische Berichte, 1924, vol. 57, p. 1620
  作者：Borsche

  DOI：——

  日期：——