cholest-5-en-3β-yl 6-<(p-tolylsulfonyl)oxy>hexyl ether | 68354-85-8

• 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: cholest-5-en-3β-yl 6-<(p-tolylsulfonyl)oxy>hexyl ether
• 英文别名: cholest-5-en-3β-yl 6-(p-toluenesulfonyloxy)hexyl ether；Cholest-5-en-3beta-yl 6-(p-toluenesulfonyloxy)hexyl ether；6-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]hexyl 4-methylbenzenesulfonate
• CAS: 68354-85-8
• 化学式: C₄₀H₆₄O₄S
• 分子量: 641.012
• InChiKey: XADPGWDVCOXNIL-PYEXXXARSA-N

物化性质

• 沸点：
  695.8±48.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  45
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cholest-5-en-3β-yl 6-<(p-tolylsulfonyl)oxy>hexyl ether 在 Bu₃P(CH₂)16CH₂Br 、 一水合肼 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 8.0h， 生成 cholest-5-en-3β-yl 6-aminohexyl ether
  参考文献：
  名称：

  Functional cholesteryl binding agents: synthesis, characterization, and evaluation of antibody binding to modified phospholipid vesicles

  摘要：

  A series of functionalized cholesteryl derivatives were synthesized. The various lipophilic protein modification agents were analyzed for their protein binding ability. The binding of human IgG, labeled with 125I, to modified phospholipid vesicles was ascertained. Two agents performed well. These were cholest-5-en-3 beta-yl 5-carboxypentyl ether succinimido ester and cholest-5-en-3 beta-yl 6-carboxyhexyl ether succinimido ester.

  DOI：

  10.1021/jm00160a004
• 作为产物：
  描述：

  [10,13-二甲基-17-(6-甲基庚烷-2-基)-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊并[a]菲-3-基] 4-甲基苯磺酸酯 在 吡啶 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 生成 cholest-5-en-3β-yl 6-<(p-tolylsulfonyl)oxy>hexyl ether
  参考文献：
  名称：

  Functional cholesteryl binding agents: synthesis, characterization, and evaluation of antibody binding to modified phospholipid vesicles

  摘要：

  A series of functionalized cholesteryl derivatives were synthesized. The various lipophilic protein modification agents were analyzed for their protein binding ability. The binding of human IgG, labeled with 125I, to modified phospholipid vesicles was ascertained. Two agents performed well. These were cholest-5-en-3 beta-yl 5-carboxypentyl ether succinimido ester and cholest-5-en-3 beta-yl 6-carboxyhexyl ether succinimido ester.

  DOI：

  10.1021/jm00160a004

文献信息

• Steroidal glycolipids as host resistance stimulators
  申请人：Merck & Co., Inc.

  公开号：US04652553A1

  公开（公告）日：1987-03-24

  Described are derivatives of glycolipids with substituted steroids bridged via a medium length hydrocarbon chain to 1-thio-D-mannopyranoses or 1-thio-L-fucopyranoses. These compounds protect an immunocompromised human or animal host against opportunistic infection by virtue of their immunostimulant properties.

  描述了通过中等长度的碳氢链连接到1-硫代-D-甘霖糖或1-硫代-L-岩藻糖的替代类固醇的糖脂衍生物。这些化合物通过其免疫刺激性能保护免疫受损的人类或动物宿主免受机会性感染的侵害。
• Steroidal glycolipids as host resistance stimulators against viral
  申请人：Merck & Co., Inc.

  公开号：US04942154A1

  公开（公告）日：1990-07-17

  Disclosed are steroidal derivatives of glycolipids, in which steroids are bridged, via a medium length hydrocarbon chain, to 1-thio-D-mannopyranoses or 1-thio-L-fucopyranoses that protect an immunocompromised host, particularly resulting from an AIDS-related virus, against opportunistic infection.

  本发明涉及甾体衍生物的糖脂类化合物，其中甾体通过中等长度的碳氢链与1-硫代-D-甘露糖苷或1-硫代-L-岩藻糖苷相连，用于保护免疫功能受损的宿主，尤其是由艾滋病相关病毒引起的，免受机会性感染的侵害。
• Steroidal glycolipids
  申请人：Merck & Co., Inc.

  公开号：US04652637A1

  公开（公告）日：1987-03-24

  Described are derivatives of glycolipids with substituted steroids bridged via a medium length hydrocarbon chain to 1-thio-D-mannopyranoses or 1-thio-L-fucopyranoses. These compounds protect an immunocompromised human or animal host against opportunistic infection by virtue of their immunostimulant properties.

  本文描述了一种通过介质长度的碳氢链桥接到1-硫基-D-甘露糖或1-硫基-L-岩藻糖的取代类固醇的糖脂衍生物。这些化合物具有免疫刺激性质，能够保护免疫系统受损的人或动物宿主免受机会性感染的侵害。
• Amphiphilic Fullerene-Cholesterol Derivatives: Synthesis and Preparation ofLangmuir andLangmuir-Blodgett Films
  作者：Delphine Felder、Maria del Pilar Carreón、Jean-Louis Gallani、Daniel Guillon、Jean-François Nierengarten、Thierry Chuard、Robert Deschenaux

  DOI：10.1002/1522-2675(20010516)84:5<1119::aid-hlca1119>3.0.co;2-3

  日期：2001.5.16

  Amphiphilic fullerene bis-adducts 11 and 14 containing two and four cholesterol moieties, respectively, were prepared starting from the corresponding bis-malonate derivatives. In a systematic study, their spreading behavior at the air-water interface was compared to that of bis-adduct 6 with no polar head-group. Compared to 6, for which some three-dimensional aggregation occurs, the polar head-group in 11 and 14 is responsible for an attractive interaction with the aqueous subphase, forcing the molecules towards the water surface into a two-dimensional arrangement. Even if homogeneous Langmuir films were obtained with both 11 and 14, only the films of 14 show a reversible compression/expansion behavior. This suggests that, by increasing the number of cholesterol subunits, the encapsulation of the C-sphere in its addend is more efficient, thus preventing fullerene-fullerene interactions and aggregation phenomena. The Langmuir films of 11 and 14 were also efficiently transferred onto hydrophilic quartz slides, yielding Langmuir-Blodgett films.
• Smectic C Phases and Reentrant Behavior in Cholesterol Containing Dimer Liquid Crystals
  作者：Antonius Marcelis、Arie Koudijs、Ernst Sudhölter

  DOI：10.1080/15421400490435035

  日期：2004.1

  A series of dodecyloxybiphenylyl and cholesteryl group containing dimers with ethers as spacers have been prepared and their liquid crystalline properties were investigated as a function of spacer length. For short spacers SmA and SmC phases were observed with monolayer ordering. This is aparent from. polarization microscopy and temperature dependent X-ray measurements. With increasing spacer length a N*-phase gradually appears whose liquid crystalline range increases. For the dodecyl spacer no smectic phase is observed anymore. For the nonyl spacer reentrant behavior is found (N*-TGB-SmA-TGB-N*). Reentrant behavior, probably N*-TGB-N*, is also observed for a related compound with an ester spacer.