cholest-5-en-3β-ol methylthiomethyl ether | 14958-40-8

• 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-ol methylthiomethyl ether
• 英文别名: 3β-(methylthiomethoxy)cholest-5-en；cholesterol methylthiomethyl ether；Cholesterylmethylthiomethylether；(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-3-(methylsulfanylmethoxy)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene
• CAS: 14958-40-8
• 化学式: C₂₉H₅₀OS
• 分子量: 446.781
• InChiKey: GWAPDYPZFCNJJC-AXYOXNHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.73
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-甲基哌啶 、 cholest-5-en-3β-ol methylthiomethyl ether 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 1,2-二氯乙烷 为溶剂， 以21%的产率得到
  参考文献：
  名称：

  Synthesis of cationic cholesterol-containing amphiphiles with an acid-labile linker

  摘要：

  The synthesis of cationic amphiphiles from cholesterol methylthiomethyl ether has been carried out.

  DOI：

  10.1016/j.mencom.2007.09.011
• 作为产物：
  描述：

  胆固醇 、 二甲基亚砜 在 溶剂黄146 作用下， 以 乙酸酐 为溶剂， 生成 cholest-5-en-3β-ol methylthiomethyl ether
  参考文献：
  名称：

  氯三甲基硅烷和乙酸酐裂解醚

  摘要：

  甲基和苄基醚已用由三甲基氯硅烷和乙酸酐组成的试剂组合裂解，其中含有催化量的浓硫酸。甲硫基甲基醚与氯代三甲基硅烷和乙酸酐产生相应的乙酰氧基甲基醚。与三氟化硼醚化物和乙酸酐方法进行醚裂解的比较研究表明，氯三甲基硅烷和乙酸酐（在H 2 SO 4催化下）可能是一种有用的替代方法。

  DOI：

  10.1016/s0040-4020(01)87555-4

文献信息

• A MILD AND CONVENIENT METHOD FOR THE PREPARATION OF METHYLTHIOMETHYL ETHERS: PROTECTION OF HYDROXYL GROUPS
  作者：Kenji Suzuki、Junji Inanaga、Masaru Yamaguchi

  DOI：10.1246/cl.1979.1277

  日期：1979.10.5

  Methylthiomethyl (MTM) ethers of various types of alcohols were prepared under mild conditions by using chloromethyl methyl sulfide and silver nitrate.

  使用氯甲基甲基硫化物和硝酸银在温和条件下制备了各种醇的甲硫基甲基（MTM）醚。
• Novel Cholesterol-Based Cationic Lipids for Gene Delivery
  作者：Darya A. Medvedeva、Mikhail A. Maslov、Roman N. Serikov、Nina G. Morozova、Galina A. Serebrenikova、Dmitry V. Sheglov、Alexander V. Latyshev、Valentin V. Vlassov、Marina A. Zenkova

  DOI：10.1021/jm901022t

  日期：2009.11.12

  Gene therapy based on gene delivery is a promising strategy for the treatment of human disease. Here we present data oil structure/biological activity of new biodegradable cholesterol-based cationic lipids with various heterocyclic cationic head groups and linker types. Enhanced accumulation of nucleic acids in the cells mediated by the lipids was demonstrated by fluorescent microscopy and flow cytometry. Light scattering and atomic force microscopy were used to find structure/transfection activity correlations for the lipids. We found that the ability of the lipids to stimulate intracellular accumulation of the oligodeoxyribonucleotides and plasmid DNA correlates well with their ability to form in solution lipid/NA complexes of sizes that do not exceed 100 nm. Screening of the lipids revealed the most promising transfection agents both in terms of low toxicity and efficient delivery: cholesterol-based lipids with positively charged pyridine and methyl imidazole head groups and either the ester or carbamate linker.
• A new method for cleaving methyl and methylthiomethyl ethers
  作者：Nabin C Barua、Ram P Sharma、Jogendra N Baruah

  DOI：10.1016/s0040-4039(00)86400-x

  日期：1983.1
• CHOWDHURY, P. K.;SHARMA, R. P.;BARUAH, J. N., TETRAHEDRON LETT., 1983, 24, N 41, 4485-4486
  作者：CHOWDHURY, P. K.、SHARMA, R. P.、BARUAH, J. N.

  DOI：——

  日期：——