caesium palmitate | 14912-92-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: caesium palmitate
• 英文别名: Cesium palmitate；Caesiumpalmitat；cesium;hexadecanoate
• CAS: 14912-92-6
• 化学式: C₁₆H₃₁O₂*Cs
• 分子量: 388.326
• InChiKey: XXJVRVRVOQTORH-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.22
• 重原子数：
  19
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  40.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  caesium palmitate 在 吡啶 、 4-二甲氨基吡啶 、 四溴化碳 、 20 % Pd(OH)2/C 、 氢气 、 溶剂黄146 、 三苯基膦 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 环己烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 37.0h， 生成 3-O-(6-O-palmitoyl-α-D-glucopyranosyl)-1,2-di-O-palmitoyl-sn-glycerol
  参考文献：
  名称：

  An easy α-glycosylation methodology for the synthesis and stereochemistry of mycoplasma α-glycolipid antigens

  摘要：

  Mycoplasma fermentans在细胞膜上具有独特的α-糖脂抗原（GGPL-I和GGPL-III），其中在糖原位（6-OH）位置携带磷胆碱基团。本文描述了一种实用的合成路径，用于合成GGPL-I同分异构体（C_16:0）及其对映异构体，其中我们有效地应用了一锅法α-糖基化方法。合成的GGPL-I同分异构体通过¹H NMR光谱表征，以确定在无环甘油部分的三种构象（gg、gt、tg）之间的平衡。发现天然的GGPL-I同分异构体在脂肪尾部周围更倾向于gt（54%）和gg（39%）构象，而在糖位周围则以相等的概率采用所有三种构象。这种特性与我们观察到的磷脂酰胆碱（DPPC）构象非常接近，表明Mycoplasma的糖脂GGPLs可能与普遍存在的磷脂一起构成细胞质膜，而不会引起立体化学应力。

  DOI：

  10.3762/bjoc.8.70
• 作为试剂：
  描述：

  丙酮缩甘油 在 N-甲基咪唑 、 四丁基碘化铵 、 caesium palmitate 、 sodium sulfate 、 三乙胺 、 2,6-二氯苯甲酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 162.5h， 生成 1,2-dipalmitoyl-sn-glycero-3-[(2′,3′-isopropylidene-rac-glycero)-1′-benzylphosphate]
  参考文献：
  名称：

  磷脂酰甘油的灵活合成方法

  摘要：

  报告了灵活的5步序列，可以合成在sn -1和sn -2位置带有不同或相同链的磷脂酰甘油。

  DOI：

  10.1002/ejoc.201701178

文献信息

• A Rapid Condensation between Lysophosphorylcholine and Fatty Acids with an Easily Separable Amine Base
  作者：Yuichi Kobayashi、Hukum P. Acharya

  DOI：10.1055/s-2005-871973

  日期：——

  With 2,6-Cl2C6H3COCl and 1-methylimidazole, the title condensation completed at room temperature within 12 hours, which is shorter time than that with the standard DCC/DMAP system. Use of easily separable 1-methylimidazole from the crude product by chromatography is an additional advantage of the present reagent system.

  以2，6-Cl2C6H3COCl和1-甲基咪唑为原料，标题缩合反应在室温下12小时内完成，时间短于标准DCC/DMAP体系。通过色谱法容易地从粗产物中分离出1-甲基咪唑，是本试剂体系的额外优势。
• Lipase-catalyzed enantioselective esterification or hydrolysis of 1-O-alkyl-3-O-tosylglycerol derivatives. Practical synthesis of (S)-(+)-1-O-hexadecyl-2,3-di-O-hexadecanoylglycerol, a marine natural product
  作者：Robert Chenevert、Rene Gagnon

  DOI：10.1021/jo00057a015

  日期：1993.2

  Racemic 1-O-alkyl-3-O-tosylglycerol derivatives were resolved by acylation with palmitic anhydride in the presence of Pseudomonas fluorescens lipase in organic media. The reverse reaction, the enzymatic hydrolysis of 1-O-alkyl-2-O-palmitoyl-3-O-tosylglycerols in isopropyl ether saturated with water was also highly stereoselective. An efficient and simple synthesis of the naturally occurring (S)-(+)-1-O-hexadecyl-2,3-di-O-hexadecanoylglycerol based on this process is reported.
• Efficient Synthesis of Phospholipids from Glycidyl Phosphates
  作者：Jan Lindberg、Johan Ekeroth、Peter Konradsson

  DOI：10.1021/jo010734+

  日期：2002.1.1

  New efficient routes to enantiopure phospholipids, starting from (S)-glycidol, are described. Lysophosphatidic acids and phosphatidic acids were obtained in good overall yields from (S)-glycidol, in only three and four steps, respectively. Moreover, the strategy can also be used to produce phosphatidylcholines in three steps. Using dialkylphosphoramidites, (S)-glycidol was phosphorylated to give (R)-1-O-glycidyl dialkyl phosphates. Regiospecific epoxide opening, using hexadecanol or cesium palmitate, followed by phosphate deprotection, provided lysophosphatidic acids. 2-O-Esterification prior to phosphate deprotection provided 1,2-O-diacyl and 1-O-alkyl-2-O-acyl phosphatidic acids. Phosphorylation of (S)-glycidol using phosphorus oxychloride followed by in situ treatment with choline tosylate produced (R)-glycidyl phosphocholine. Subsequent nucleophilic opening of the epoxide using cesium palmitate produced 1-O-palmitoyl-sn-glycero-3-phosphocholine, which has been used in syntheses of phosphatidylcholines.
• Efficient Syntheses of Pure Mixed Triglycerides
  作者：Jean-Louis Gras、Jean-François Bonfanti

  DOI：10.1080/00397910008087042

  日期：2000.12

  Pure mixed triglycerides can be prepared from diglycerides and by acylolysis of glycerolformal tosylate without isomerization. The last fatty chain, with or without a functional group, can be introduced on any position of glycerol.
• Palmitates of Isomeric 15-Oxygenated Δ8(14)-Sterols
  作者：D. V. Ignatov、Yu. I. Prokof'ev、V. P. Timofeev、A. Yu. Misharin

  DOI：10.1023/b:rubi.0000023106.52513.6a

  日期：2004.3

  3beta-Hexadecanoyloxy-5alpha-cholest-8(14)-en-15-one, 3alpha-hexadecanoyloxy-5alpha-cholest-8(14)-en-15-one, 15beta-hexadecanoyloxy-5alpha-cholest-8(14)-en-3beta-ol, 15alpha-hexadecanoyloxy-5alpha-cholest-8(14)-en-3beta-ol, 15beta-hexadecanoyloxy-5alpha-cholest-8(14)-en-3-one, and 15alpha-hexadecanoyloxy-5alpha-cholest-8(14)-en-3-one were synthesized and their chromatographic and H-1 NMR characteristics were determined.