1-palmitoyl-2-(15-hexadecyn-1-oyl)-3-(4-methoxybenzyl)-sn-glycerol | 139100-84-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1-palmitoyl-2-(15-hexadecyn-1-oyl)-3-(4-methoxybenzyl)-sn-glycerol
• 英文别名: [(2S)-2-hexadec-15-ynoyloxy-3-[(4-methoxyphenyl)methoxy]propyl] hexadecanoate
• CAS: 139100-84-8
• 化学式: C₄₃H₇₂O₆
• 分子量: 685.041
• InChiKey: ZJBPRRAJYSZXKB-RWYGWLOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.85
• 重原子数：
  49.0
• 可旋转键数：
  35.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-palmitoyl-2-(15-hexadecyn-1-oyl)-3-(4-methoxybenzyl)-sn-glycerol 在 吡啶 、 copper diacetate 作用下， 反应 2.0h， 以68%的产率得到2,2'-(15,17-dotriacontadiyne-1,32-dioyl)bis(1-palmitoyl-3-(4-methoxybenzyl)-sn-glycerol)
  参考文献：
  名称：

  A new reagent for the removal of the 4-methoxybenzyl ether: application to the synthesis of unusual macrocyclic and bolaform phosphatidylcholines.

  摘要：

  The total synthesis of two novel polymerizable phosphatidylcholines has been accomplished using 3-(4-methoxybenzyl)-sn-glycerol 10 as starting material. Diacylation of 10 with 13-tetradecynoic acid followed by oxidative coupling of the alkynes gives the 32-membered glycerol macrocycle 17. Sequential acylation of 10 with palmitic acid and 15-hexadecynoic acid followed by oxidative coupling gives the bolaform 16, tethered at the 2-position of the glycerol. A new method for the cleavage of 4-methoxybenzyl ethers using dimethylboron bromide at -78-degrees-C in dichloromethane is described. 1,3-Diacetylenes, 1,4-dienes, and esters are stable under the experimental conditions, and the migration of acyl chains from secondary to primary positions is totally suppressed. The diacylglycerols are then efficiently converted into the corresponding phosphatidylcholines by tetrazole-catalyzed phosphitylation with 2-cyanoethyl 2-bromoethyl N,N-diisopropylamino phosphite, oxidation, and treatment with trimethylamine to simultaneously displace the bromide and eliminate the cyanoethyl group.

  DOI：

  10.1021/jo00032a033
• 作为产物：
  描述：

  7-十六-1-醇 在 4-二甲氨基吡啶 、 jones' reagent 、 potassium tert-butylate 、 lithium 、 1,3-丙二胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 5.75h， 生成 1-palmitoyl-2-(15-hexadecyn-1-oyl)-3-(4-methoxybenzyl)-sn-glycerol
  参考文献：
  名称：

  A new reagent for the removal of the 4-methoxybenzyl ether: application to the synthesis of unusual macrocyclic and bolaform phosphatidylcholines.

  摘要：

  The total synthesis of two novel polymerizable phosphatidylcholines has been accomplished using 3-(4-methoxybenzyl)-sn-glycerol 10 as starting material. Diacylation of 10 with 13-tetradecynoic acid followed by oxidative coupling of the alkynes gives the 32-membered glycerol macrocycle 17. Sequential acylation of 10 with palmitic acid and 15-hexadecynoic acid followed by oxidative coupling gives the bolaform 16, tethered at the 2-position of the glycerol. A new method for the cleavage of 4-methoxybenzyl ethers using dimethylboron bromide at -78-degrees-C in dichloromethane is described. 1,3-Diacetylenes, 1,4-dienes, and esters are stable under the experimental conditions, and the migration of acyl chains from secondary to primary positions is totally suppressed. The diacylglycerols are then efficiently converted into the corresponding phosphatidylcholines by tetrazole-catalyzed phosphitylation with 2-cyanoethyl 2-bromoethyl N,N-diisopropylamino phosphite, oxidation, and treatment with trimethylamine to simultaneously displace the bromide and eliminate the cyanoethyl group.

  DOI：

  10.1021/jo00032a033