1-palmitoyl-3-(4-methoxybenzyl)-sn-glycerol | 139100-83-7

• 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-3-(4-methoxybenzyl)-sn-glycerol
• 英文别名: [(2S)-2-hydroxy-3-[(4-methoxyphenyl)methoxy]propyl] hexadecanoate
• CAS: 139100-83-7
• 化学式: C₂₇H₄₆O₅
• 分子量: 450.659
• InChiKey: RHULDEIMIZCOLL-VWLOTQADSA-N

物化性质

• 沸点：
  559.8±45.0 °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

• 作为反应物：
  描述：

  1-palmitoyl-3-(4-methoxybenzyl)-sn-glycerol 在 W-4 Raney nickel 氢气 、 双氧水 、 N,N-二异丙基乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 43.25h， 生成 O-<2-(N-(tert-butyloxycarbonyl)amino)ethyl> O-methyl O-(1'-O-palmitoyl-sn-3'-glyceryl) phosphate
  参考文献：
  名称：

  General Method for the Synthesis of Phospholipid Derivatives of 1,2-O-Diacyl-sn-Glycerols

  摘要：

  An efficient phosphite coupling protocol is described for the syntheses of the major classes of phospholipids that are derived from 1,2-O-diacyl-sn-glycerols and analogues thereof. The symmetrical diacyl glycerols 10c,d were prepared by straightforward acylation of 3-O-benzyl-sn-glycerol (7) with the appropriate carboxylic acid in the presence of dicyclohexylcarbodiimide (DCC) and 4-(dimethylamino)pyridine (DMAP). A simple method for preparing saturated and unstaturated mixed 1,2-O-diacyl-sn-glycerols was then devised that involved stepwise acylation of 7 with different alkyl carboxylic acids and debenzylation this procedure is exemplified by the preparation of 10a,b. The 1,2-O-diacyl-sn-glycerols 10a-d were then coupled with suitably protected lipid head groups employing reactive alkyl or aryl dichlorophosphites to give intermediate phosphite triesters in high overall yields. Oxidation or sulfurization of these phosphites proceeded smoothly to give the corresponding phosphate or phosphorothioate triesters, deprotection of which then provided the phosphatidylcholines 16 and 17, the phosphatidylethanolamine 20, the phosphatidylserine 28, and the phosphatidylinositols 37 and 38. Preparation of 37 and 38 required the invention of an improved method for resolving the isopropylidene-protected D-myo-inositol derivative 33. This phosphite coupling procedure was modified to assemble phospholipids bearing-polyunsaturated acyl side chains at the sn-2-position as exemplified by the preparation of the phosphatidylethanolamine 26. The one-pot phosphite coupling procedure is also applicable to the syntheses of a variety of other biologically interesting phospholipid analogues. For example, the phosphatidylinositol analogues 49-51, in which the hydroxyl group at C(2) of the inositol ring has been modified, were prepared in excellent overall yields by conjoining the 1,2-O-diacyl-sn-glycerol 10c with the protected inositol derivatives 44, 45, and 48. Phospholipid analogues that contain other replacements of the phosphate group including phosphoramidates and thiophosphates maybe prepared as evidenced by the syntheses of 56 and 61 in which the sn-3 oxygen atom of the 1,2-O-diacyl-sn-glycerol moiety is replaced with an N-benzyl group or a sulfur atom, respectively.

  DOI：

  10.1021/jo00096a023
• 作为产物：
  描述：

  (S)-4-[(4-methoxybenzyloxy)methyl]-2,2-dimethyl-1,3-dioxolane 在 盐酸 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 18.0h， 生成 1-palmitoyl-3-(4-methoxybenzyl)-sn-glycerol
  参考文献：
  名称：

  含不对称酰基链的磷脂酰甘油的合成使用 H-膦酸盐方法

  摘要：

  天然存在的磷脂，如磷脂酰甘油 (PG)，因其在疾病机制中发挥的作用而受到关注。为了阐明 PG 的代谢，需要一种光学纯材料，但不幸的是，这种材料无法在市场上买到。我们之前的 PG 合成路线使用亚磷酰胺方法，解决了在头基磷酸化之前围绕脂肪酸底物范围和甘油主链修饰的问题，但由于纯化挑战，整个途径的可重复性步履蹒跚。在此，我们利用具有色谱友好且稳定的三乙基铵 H-膦酸盐的 H-膦酸盐，提出了一种通过更少的步骤获得光学纯 PG 的稳健途径。我们的路线也适用于同时安装不同的酰基链，

  DOI：

  10.3390/molecules27072199

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。
• The key entity of a DCAR agonist, phosphatidylinositol mannoside Ac₁PIM₁: its synthesis and immunomodulatory function
  作者：Yohei Arai、Shota Torigoe、Takanori Matsumaru、Sho Yamasaki、Yukari Fujimoto

  DOI：10.1039/c9ob02724f

  日期：——

  Ac1PIM1 is a potential biosynthetic intermediate for phosphatidylinositol mannosides (PIMs) from Mycobacterium tuberculosis. We achieved the first synthesis of Ac1PIM1 by utilizing an allyl-type protecting group strategy and regioselective phosphorylation of inositol. A very potent agonist of an innate immune receptor DCAR, which is better than previously known agonists, is demonstrated.

  Ac1PIM1是来自结核分枝杆菌的磷脂酰肌醇甘露糖苷（PIM）的潜在生物合成中间体。我们通过利用烯丙基型保护基策略和肌醇的区域选择性磷酸化实现了Ac1PIM1的首次合成。证明了先天免疫受体DCAR的非常有效的激动剂，其比以前已知的激动剂更好。
• Antithrombogenic membrane mimetic compositions and methods
  申请人：——

  公开号：US20040073295A1

  公开（公告）日：2004-04-15

  The present Specification describes materials and methods which provide for improved performance of medical prostheses, including vascular graft material, artificial heart valves, and other implanted materials. The materials comprising bound thrombomodulin or a functionally equivalent derivative protein, provide for fewer undesirable side effects including inflammation, thromboses and neointimal hyperplasia.

  本说明书描述的材料和方法可改善医疗假体的性能，包括血管移植材料、人工心脏瓣膜和其他植入材料。包含结合血栓调节蛋白或功能相当的衍生物蛋白的材料可减少不良副作用，包括炎症、血栓形成和新内膜增生。
• Synthesis of Isoprostanyl Phosphatidylcholine and Isoprostanyl Phosphatidylethanolamine
  作者：Manami Shizuka、Thomas O. Schrader、Marc L. Snapper

  DOI：10.1021/jo0518553

  日期：2006.2.1

  The syntheses of two isoprostanyl phospholipids are described. A newly established route to 15-F-2t-isoprostane and ent-15-epi-F-2t-isoprostane has allowed for the selective preparation of 15-F-2t-isoprostanyl phosphatidylethanolamine and ent-15-epi-F-2t-isoprostanyl phosphatidylcholine. The nature of the head-groups dictates the coupling strategy used to attach the appropriately protected isoprostanes to the corresponding lysophospholipids. Preliminary H-1 NMR and P-31 NMR studies indicate that these isoprostanyl phospholipids aggregate in apolar solvents.
• A new reagent for the removal of the 4-methoxybenzyl ether: application to the synthesis of unusual macrocyclic and bolaform phosphatidylcholines.
  作者：Normand Hebert、Alain Beck、R. Bruce Lennox、George Just

  DOI：10.1021/jo00032a033

  日期：1992.3

  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.