(ethyl carbonic) (R)-4-((3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic anhydride | 85954-17-2

• 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: (ethyl carbonic) (R)-4-((3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic anhydride
• CAS: 85954-17-2
• 化学式: C₂₇H₄₄O₆
• 分子量: 464.643
• InChiKey: XJMULCYVTMTWSN-IOJOMAJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.09
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  93.06
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (ethyl carbonic) (R)-4-((3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic anhydride 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲苯 为溶剂， 反应 42.0h， 生成 3-(3,5-dichlorophenyl)carbamoyl-12-(3,5-dimethylphenyl)carbamoyl-N-allyl-deoxycholan-24-amide
  参考文献：
  名称：

  Synthesis of a new family of four deoxycholic acid derived chiral stationary phases and their evaluation in the HPLC resolution of racemic compounds

  摘要：

  Four new chiral selectors obtained by suitable derivatization of the hydroxyl groups of the deoxycholic acid with two identical (homoderivatized) or different (heteroderivatized) arylisocyanates have been prepared and linked covalently to silica gel to obtain new chiral stationary phases (CSPs) for the HPLC separation of enantiomers. The CSPs containing two identical substituents are able to enantiodiscriminate different classes of racemic compounds, or the same racemates to a different extent, a property which depends on the different electronic character of the arylcarbamate moieties. The heteroderivatized CSPs retain the character of the two homoderivatized phases: however, the relative position of the two different arylcarbamate moieties on the deoxycholic backbone strongly affects the enantiodiscrimination capability of these two CSPs. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00337-7
• 作为产物：
  描述：

  去氧胆酸 、 氯甲酸乙酯 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 生成 (ethyl carbonic) (R)-4-((3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic anhydride
  参考文献：
  名称：

  胆汁酸和氨基酸结合物的超分子凝胶及其应用

  摘要：

  由低分子量分子组成的水凝胶在生物医学应用中越来越重要。在这项工作中，我们报告了从胆汁酸-氨基酸缀合物形成可注射水凝胶。水凝胶化能力取决于多种因素，例如胆汁酸骨架、胆汁酸和氨基酸之间的连接以及 pH 值。我们已经表明凝胶特性取决于多种非共价相互作用以及分子疏水和亲水特性之间的平衡。还测定并比较了石胆酰-L-苯丙氨酸、石胆酰甘氨酸、石胆酰-L-缬氨酸和石胆酰-L-丙氨酸的晶体结构。最后，利用刚性水凝胶框架生产具有金和氧化锌纳米颗粒的无机-有机复合材料。

  DOI：

  10.1002/ejoc.201601616

文献信息

• Synthesis of nucleoside and nucleotide conjugates of bile acids, and polymerase construction of bile acid-functionalized DNA
  作者：Satu Ikonen、Hana Macíčková-Cahová、Radek Pohl、Miloslav Šanda、Michal Hocek

  DOI：10.1039/b924072a

  日期：——

  Sonogashira cross-coupling reactions of 5-iodopyrimidine or 7-iodo-7-deazaadenine nucleosides with bile acid-derived terminal acetylenes linked via an ester or amide tether gave the corresponding bile acid–nucleoside conjugates. Analogous reactions of halogenated nucleoside triphosphates gave directly bile acid-modified dNTPs. Enzymatic incorporation of these modified nucleotides to DNA was successfully

  Sonogashira的水交叉偶联反应 5-碘嘧啶带有胆汁酸衍生的末端乙炔的7-iodo-7-deazaadenine核苷通过酯或酰胺系链连接在一起，得到了相应的胆汁酸-核苷共轭物。卤代核苷三磷酸的类似反应直接得到胆汁酸修饰的dNTP。使用Phusion聚合酶进行引物延伸，成功地将这些修饰的核苷酸酶促掺入DNA。dNTP之一（dCTP 轴承 胆酸）对于PCR扩增也是有效的。
• Systematic Modulation of the Supramolecular Gelation Properties of Bile Acid Alkyl Amides
  作者：Riikka Kuosmanen、Rakesh Puttreddy、Kari Rissanen、Elina Sievänen

  DOI：10.1002/chem.201803151

  日期：2018.12.12

  based on bile acid alkyl amides were studied in detail. Based on the results, the number of hydroxyl groups attached to the steroidal backbone plays a major role in the gelation, although the nature of the aliphatic side chain also modulates the gelation abilities. Of the 50 gel systems studied, 35 are based on lithocholic acid and 15 on cholic acid derivatives. The deoxycholic acid derivatives did

  详细研究了九种基于胆酸烷基酰胺的低分子量胶凝剂（LMWG）的自组装性能。基于该结果，尽管脂族侧链的性质也调节了凝胶化能力，但是连接至甾族骨架的羟基数目在凝胶化中起着重要作用。在研究的50种凝胶体系中，有35种基于石胆酸，而15种基于胆酸衍生物。脱氧胆酸衍生物没有形成任何凝胶。凝胶化主要发生在芳族溶剂中，并且凝胶表现出典型的纤维或球形形态。在13在结晶材料和相应的湿有机凝胶上测得的C交叉极化魔角旋转（CPMAS）NMR光谱是相似的，这表明两种材料中发现的化学环境（即分子间相互作用）相似。研究的所有九种胆酸酰胺衍生物的单晶X射线结构揭示了固态中非常相似的分子构象，并洞悉了凝胶态下可能的分子间相互作用。
• Conjugation of Small Molecules to RNA Using a Reducible Disulfide Linker Attached at the 2′-OH Position through a Carbamate Function
  作者：Florian Gauthier、Astrid Malher、Jean-Jacques Vasseur、Christelle Dupouy、Françoise Debart

  DOI：10.1002/ejoc.201900740

  日期：2019.9.8

  In this paper, we developed a post‐synthesis conjugation of small molecules to RNA using a reduction sensitive disulfide linker connected to 2′OH through a carbamate function.

  在本文中，我们使用还原敏感性二硫键通过氨基甲酸酯功能连接到2'OH，开发了小分子与RNA的合成后缀合。
• Self-assembly properties of bile acid derivatives of <scp>l</scp>-cysteine, <scp>l</scp>-valine and <scp>l</scp>-serine alkyl esters
  作者：Virpi Noponen、Arto Valkonen、Manu Lahtinen、Hannu Salo、Elina Sievänen

  DOI：10.1080/10610278.2012.735365

  日期：2013.3.1

  Comprehensive self-assembly studies for nine bile acid amides of amino acid esters are reported. The number of the hydroxyl groups attached to the steroidal skeleton and the character of the amino acid ester moiety were used as variables when examining the self-assembly properties of the compounds. Two of the compounds were shown to undergo self-assembly leading to organogelation. In addition, preliminary

  报告了氨基酸酯的九种胆汁酸酰胺的综合自组装研究。在检查化合物的自组装特性时，将连接到甾体骨架上的羟基数量和氨基酸酯部分的特征用作变量。其中两种化合物显示出自组装导致有机凝胶化。此外，在极性有机溶剂的水性混合物中进行了初步自组装研究。为了更深入地了解自组装结构，使用了显微方法（光学显微镜和扫描电子显微镜）。此外，解决了三种化合物的单晶 X 射线结构。
• 라이신-데옥시콜산 염의 제조 방법
  申请人：ICURE BNP Co., Ltd 주식회사 아이큐어비앤피(120180092192) Corp. No ▼ 134111-0435649BRN ▼696-86-00315

  公开号：KR20210092883A

  公开（公告）日：2021-07-27

  본 발명은 라이신-데옥시콜산 염의 제조 방법에 대한 것으로서, 라이신-데옥시콜산 염의 제조 방법은 포스파이트(phosphite)계 화합물 또는 아실 할라이드(acyl halide)계 화합물의 존재 하에서, 데옥시콜산(deoxycholic acid, DOCA)과 라이신(lysine, Lys) 염을 커플링 반응시키는 단계를 포함한다. 본 발명의 라이신-데옥시콜산 염의 제조 방법은 고순도의 라이신-데옥시콜산 염을 경제적이고 효율적으로 제조할 수 있다.

  This invention relates to a method for producing lysine-deoxycholic acid salt, wherein the method includes a step of coupling deoxycholic acid (DOCA) and lysine (Lys) salt in the presence of a phosphite compound or an acyl halide compound. The method for producing lysine-deoxycholic acid salt of the present invention can economically and efficiently produce high-purity lysine-deoxycholic acid salt.