2-palmitoyl-3-(4-methoxybenzyl)-sn-glycerol | 139100-94-0

• 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: 2-palmitoyl-3-(4-methoxybenzyl)-sn-glycerol
• 英文别名: [(2R)-1-hydroxy-3-[(4-methoxyphenyl)methoxy]propan-2-yl] hexadecanoate
• CAS: 139100-94-0
• 化学式: C₂₇H₄₆O₅
• 分子量: 450.659
• InChiKey: HSXPBRCWYHGHOB-AREMUKBSSA-N

物化性质

• 沸点：
  559.8±40.0 °C(Predicted)
• 密度：
  0.998±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  32
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 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 2-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

文献信息

• NOVEL PHOSPHATIDYLALKANOLS AND COMPOSITIONS THEREOF
  申请人：PETHMARK AB

  公开号：US20160052946A1

  公开（公告）日：2016-02-25

  The present invention discloses a composition comprising a compound of formula I and a deuterated solvent. The deuterated solvent is miscible with water in any proportion at a temperature of 20 to 25° C. and comprises less than 5% residual 1 H-isotopes. The concentration of the compound of formula I may advantageously be determined by 1 H-QNMR. Methods of production of the composition and salts of compounds of formula I, as well as related analogs and novel reagents and intermediates for the production thereof, are also described.

  本发明揭示了一种包含式I化合物和氘化溶剂的组合物。氘化溶剂在20至25°C温度下与水可任意比例混合，并且含有少于5%的残留1H同位素。化合物式I的浓度可优选通过1H-QNMR确定。还描述了该组合物的生产方法、式I化合物的盐、以及相关类似物和新型试剂和中间体的生产方法。
• US9499572B2
  申请人：——

  公开号：US9499572B2

  公开（公告）日：2016-11-22
• US9784701B2
  申请人：——

  公开号：US9784701B2

  公开（公告）日：2017-10-10