succinic acid mono-3β-cholestanyl ester | 84597-57-9

• 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: succinic acid mono-3β-cholestanyl ester
• 英文别名: mono-3β-cholestanyl succinate；succinic acid mono-(5α-cholestan-3β-yl ester)；Bernsteinsaeure-mono-(5α-cholestan-3β-ylester)；Bernsteinsaeure-mono-[(10S)-10r.13c-dimethyl-17c-((R)-1.5-dimethyl-hexyl)-(5tH.8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthrenyl-(3c)-ester]；Bernsteinsaeure-mono-(5α-cholestanyl-(3β)-ester)；5α-Cholestanyl-(3β)-hydrogensuccinat；4-[[(3S,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4-oxobutanoic acid
• CAS: 84597-57-9
• 化学式: C₃₁H₅₂O₄
• 分子量: 488.751
• InChiKey: MVRFYLUIYUCBDW-JCOVCWPBSA-N

物化性质

• 沸点：
  578.1±33.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  succinic acid mono-3β-cholestanyl ester 在 dicyclohexylammonium (2-methyl-1-indolyl)acetate 、 硫氰酸铵 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 74.0h， 生成 H-Lys(Boc)-4-(hydroxymethyl)benzyl 3β-cholestanyl succinate
  参考文献：
  名称：

  Potentiation of the tolerogenicity of benzylpenicilloylated eicosa-L-lysine by conjugation with 4-methoxybenzyl 3.beta.-cholestanyl succinate

  摘要：

  It was previously found that amino acid polymers such as oligolysines bearing haptenic groups in high densities efficiently suppress anti-hapten IgE antibody formation. Such conjugates are strong elicitors of anaphylaxis and therefore may not be used for desensitization of drug allergic patients. Here we report on the synthesis and immunological evaluation of benzylpenicilloylated (BPO) eicosa-L-lysines containing none, one, or two lipophilic p-(hydroxymethyl)benzyl cholestan-3 beta-yl succinate (OSuco) groups. The lipophilic derivatives suppress primary as well as ongoing anti-BPO IgE antibody formation in mice much more efficiently than their hydrophilic counterpart. The lipophilic but not the hydrophilic derivatives form stable micelles in water and suppress the antibody formation according to different cellular mechanisms. The relationship between structure, hydrophobicity, and mode of action is discussed.

  DOI：

  10.1021/jm00377a020
• 作为产物：
  描述：

  5-Alpha-胆甾烷-3-酮 在 吡啶 、 乙醇 、 sodium ethanolate 作用下， 生成 succinic acid mono-3β-cholestanyl ester
  参考文献：
  名称：

  Calculating Canonical Distinguished Involutions in the Affine Weyl Groups

  摘要：

  Distinguished involutions in the affine Weyl groups, defined by G. Lusztig, play an essential role in the Kazhdan-Lusztig combinatorics of these groups. A distinguished involution is called canonical if it is the shortest element in its double coset with respect to the finite Weyl group. Each two-sided cell in the affine Weyl group contains precisely one canonical distinguished involution. We calculate the canonical distinguished involutions in the affine Weyl groups of rank less than or equal to 7. We also prove some partial results relating canonical distinguished involutions and Dynkin's diagrams of the nilpotent orbits in the Langlands dual group.

  DOI：

  10.1080/10586458.2002.10504473

文献信息

• Synthesis of Core-class 2<i>O</i>-Linked Glycopeptides: a Benzyl-protected Tetrasaccharyl Serine and its Derivative Carrying a Hydrophobic Cholestanyl Group
  作者：Jun WATABE、Latika SINGH、Yuko NAKAHARA、Yukishige ITO、Hironobu HOJO、Yoshiaki NAKAHARA

  DOI：10.1271/bbb.66.1904

  日期：2002.1

  A core-class 2 tetrasaccharide-linked serine was synthesized in a convergent manner. The coupling reaction of disaccharide glycosyl donor 3 and acceptor 4 stereoselectively afforded tetrasaccharide 15, which was converted to glycosyl fluoride 20. Glycosylation of Fmoc serine allyl ester 5 with 20 produced α- and β-glycosides in 40% and 33% yields, respectively. α-Isomer 21 was converted into 1, a useful building block for the solid-phase synthesis of glycopeptides. On the other hand, 21 was N-deprotected and condensed with hydrophobic cholestanol through a succinyl spacer. The same compound was alternatively synthesized by coupling 20 and 28. Functional group manipulation and hydrogenation afforded core 2 tetrasaccharide-cholestanol conjugate 2.

  一种核心类2的四糖链接丝氨酸以汇聚方式合成。双糖糖基给体3与受体4的偶联反应立体选择性地合成了四糖15，随后将其转化为糖基氟化物20。用20对Fmoc丝氨酸烯丙酯5进行糖基化反应分别以40%和33%的产率得到了α-和β-糖苷。α异构体21被转化为1，这是固相合成糖肽的有用构建模块。另一方面，21进行了N-脱保护，并通过琥珀酰间隔基与疏水的胆固醇醇缩合。同样，该化合物也可通过20与28的偶联反应来合成。功能基团的操控和氢化得到了核心2四糖-胆固醇醇结合物2。
• 1위 치환 3,5―디아미노벤젠의 제조 방법 및, 이에 사용되는 화합물 및 그의 제조 방법
  申请人：JSR CORPORATION 제이에스알 가부시끼가이샤(519980958416)

  公开号：KR101685400B1

  公开（公告）日：2016-12-12

  (과제) 1위 치환 3,5―디아미노벤젠을 손쉽고, 또한 안전하게 제조하기 위한 방법을 제공한다. (해결 수단) 상기 과제는 하기식 (1)로 표시되는 화합물을 1위 치환 3,5―디아미노벤젠의 제조에 사용함으로써 달성된다. <화학식 1> (식 (1) 중, R은 수소 원자, 탄소수 1∼20의 알킬기, 탄소수 6∼20의 아릴기 또는 탄소수 7∼20의 아르알킬기이며, 여기에서, 기 ―N(CH2-CH＝CHR)2가 갖는 수소 원자는 탄소수 1∼20의 알킬기로 치환될 수도 있다.)

  (问题）提供一种简便、安全地制备单取代 3,5-二氨基苯的方法。(解决方法）通过使用下式（1）所代表的化合物制备单取代的 3,5-二氨基苯来实现上述问题。<方案1>（在式（1）中，R是氢原子、碳原子数为1～20的烷基、碳原子数为6～20的芳基或碳原子数为7～20的芳烷基，其中具有基团-N(CH2-CH＝CHR)2的氢原子可被碳原子数为1～20的烷基取代）。
• Molecular engineering of liquid crystalline derivatives of 6-oxoverdazyl
  作者：Piotr Kaszynski、Marcin Jasiński、Sylwia Ciastek、Szymon Kapuscinski、Krzysztof Gebicki

  DOI：10.3998/ark.5550190.p009.800

  日期：——

  available positions on the heterocycle can be substituted with wedge-shaped or rod-like groups in combination with a small substituent, which leads to different molecular architectures and diverse organization of the mesophase. Several of these architectures have been realized experimentally and materials exhibiting columnar and calamitic phases have been obtained. Compounds with some other combination of

  6-Oxoverdazyl 是一种 π 离域稳定自由基，被认为是顺磁性自组织材料的中心结构元素。杂环上的三个可用位置可以被楔形或棒状基团取代，并结合一个小的取代基，从而导致不同的分子结构和中间相的不同组织。这些结构中的一些已经通过实验实现，并且已经获得了表现出柱状和棒状相的材料。具有一些其他取代基组合的化合物没有表现出液晶行为。该分析还指出了一些可能适合形成液晶相的新分子结构。最后，讨论了盘状衍生物的磁化率和光伏测量结果。
• On the Epimeric 7-Hydroxycholesterols
  作者：O. Wintersteiner、William L. Ruigh

  DOI：10.1021/ja01262a067

  日期：1942.10
• Potentiation of the tolerogenicity of benzylpenicilloylated eicosa-L-lysine by conjugation with 4-methoxybenzyl 3.beta.-cholestanyl succinate
  作者：Immanuel F. Luescher

  DOI：10.1021/jm00377a020

  日期：1984.11

  It was previously found that amino acid polymers such as oligolysines bearing haptenic groups in high densities efficiently suppress anti-hapten IgE antibody formation. Such conjugates are strong elicitors of anaphylaxis and therefore may not be used for desensitization of drug allergic patients. Here we report on the synthesis and immunological evaluation of benzylpenicilloylated (BPO) eicosa-L-lysines containing none, one, or two lipophilic p-(hydroxymethyl)benzyl cholestan-3 beta-yl succinate (OSuco) groups. The lipophilic derivatives suppress primary as well as ongoing anti-BPO IgE antibody formation in mice much more efficiently than their hydrophilic counterpart. The lipophilic but not the hydrophilic derivatives form stable micelles in water and suppress the antibody formation according to different cellular mechanisms. The relationship between structure, hydrophobicity, and mode of action is discussed.