1-O-hexadecyl-2-O-hexadecanoyl-3-O-p-toluenesulfonylglycerol | 146727-89-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-O-hexadecyl-2-O-hexadecanoyl-3-O-p-toluenesulfonylglycerol
• 英文别名: rac-1-hexadecyl-2-palmitoyl-3-tosylglycerol；[1-Hexadecoxy-3-(4-methylphenyl)sulfonyloxypropan-2-yl] hexadecanoate
• CAS: 146727-89-1
• 化学式: C₄₂H₇₆O₆S
• 分子量: 709.128
• InChiKey: CYBBGWVTTUDWPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.5
• 重原子数：
  49
• 可旋转键数：
  37
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-O-hexadecyl-2-O-hexadecanoyl-3-O-p-toluenesulfonylglycerol 在 水 作用下， 以 异丙醚 为溶剂， 反应 25.0h， 以44%的产率得到3-hexadecyloxy-2R-hydroxypropyl 1-para-toluenesulphonate
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo00057a015
• 作为产物：
  描述：

  溴代十六烷 在 吡啶 、 4-二甲氨基吡啶 、 四丁基碘化铵 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 101.0h， 生成 1-O-hexadecyl-2-O-hexadecanoyl-3-O-p-toluenesulfonylglycerol
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo00057a015

文献信息

• Morozova, N. G.; Andronova, I. G.; Novichkov, I. D., Russian Journal of Bioorganic Chemistry, 1993, vol. 19, # 2, p. 134 - 138
  作者：Morozova, N. G.、Andronova, I. G.、Novichkov, I. D.、Chupin, V. V.、Anikin, M. V.、Serebrinnikova, G. A.

  DOI：——

  日期：——
• 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.