1-palmitoyl-3-O-trityl-rac-glycerol | 69256-58-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-palmitoyl-3-O-trityl-rac-glycerol
• 英文别名: (+/-)-3-triphenylmethoxy-1-palmitoyloxy-propanol-(2)；(+/-)-Palmitinsaeure-(2-hydroxy-3-triphenylmethoxy-propylester)；(+/-)-2-Hydroxy-3-triphenylmethoxy-1-palmitoyloxy-propan；(+/-)-Palmitinsaeure-(2-hydroxy-3-trityloxy-propylester)；1-palmitoyl-3-trityl-glycerol；1-O-Palmitoyl-3-O-trityl-sn-glycerin；(2-hydroxy-3-trityloxypropyl) hexadecanoate
• CAS: 69256-58-2
• 化学式: C₃₈H₅₂O₄
• 分子量: 572.828
• InChiKey: WLNBLCYKJIDPRR-UHFFFAOYSA-N

物化性质

• 沸点：
  680.2±55.0 °C(Predicted)
• 密度：
  1.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  42
• 可旋转键数：
  23
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-palmitoyl-3-O-trityl-rac-glycerol 在 4-二甲氨基吡啶 、 硼酸 、 silica gel 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醚 、 二氯甲烷 、 Petroleum ether 为溶剂， 生成 1-palmitoyl-2-<3-(3-amino-2,4,6-triiodophenyl)propanoyl>-rac-glycerol
  参考文献：
  名称：

  Synthesis and evaluation of iodinated analogs of diacylglycerols as potential probes for protein kinase C

  摘要：

  Analogues of diacylglycerol containing a 3-(3-amino-2,4,6-triiodophenyl)-2-ethylpropanoyl or 3-(3-amino-2,4,6-triiodophenyl)propanoyl group in the 2-position (1a and 1b, respectively) were synthesized and shown to compete with [3H]phorbol dibutyrate [( 3H]PDBu) for binding in a crude rat brain preparation. Phorbol diesters have been shown to bind specifically to protein kinase C and the PDBu receptor has been copurified with protein kinase C activity. The four diastereomers of 1a (1c-f) were synthesized from chiral starting material and studied in the same assay. The affinities for the [3H]PDBu binding site of 1a, 1b, and two isomers of 1a with naturally occurring L configuration were comparable to that of 1-oleoyl-2-acetyl-rac-glycerol (OAG), but the D isomers of 1a were essentially inactive. The chirality of the side chain did not influence the binding affinity. Activation of protein kinase C by 1a, 1c, and 1e demonstrated the same stereochemical requirements, but none were as active as OAG. For the 1,3-isomers 2, 2a, and 2b, the competitive binding studies gave different results. The racemic mixture and the D isomer, 2b, were able to compete for binding, but the L isomer, 2a, did not compete. These studies demonstrate that diacylglycerol binding to and activation of protein kinase C is stereospecific for the glycerol backbone, but not the side chain. Furthermore, the D-1,3-isomer must exist in a conformation such that the acyl and hydroxyl oxygens assume a spatial relationship similar to that in the L-1,2-isomers.

  DOI：

  10.1021/jm00123a024
• 作为产物：
  描述：

  甘油棕榈酸酯 以100的产率得到1-palmitoyl-3-O-trityl-rac-glycerol
  参考文献：
  名称：

  Preparation of glycerol derivatives and intermediates therefor

  摘要：

  本发明揭示了一种高效率和高产率的选择区域性制备甘油衍生物的方法。该选择区域性制备1-R1-2-R2-3-乙酰基-甘油衍生物的方法包括以下步骤：通过在1-R1-甘油的3位引入保护基获得1-R1-3-保护基-甘油；通过在1-R1-3-保护基-甘油的2位引入R2基团获得1-R1-2-R2-3-保护基-甘油；同时进行去保护反应和乙酰化反应，制备1-R1-2-R2-3-保护基-甘油。其中，R1和R2是具有16到22个碳原子的脂肪酸基团，且彼此不同；保护基为三苯甲基基团或三烷基硅基团。

  公开号：

  US07868196B2

文献信息

• Preparation of glycerol derivatives ad intermediates therefor
  申请人：Lee Tae-Suk

  公开号：US20090253923A1

  公开（公告）日：2009-10-08

  Disclosed is a process for the regioselective preparation of glycerol derivative in a high efficiency and yield. The process for the regioselective preparation of 1-R 1 -2-R 2 -3-acetyl-glycerol derivative comprises the steps of: obtaining 1-R 1 -3-protecting group-glycerol by introducing a protecting group to 3-position of 1-R 1 -glycerol; obtaining 1-R 1 -2-R 2 -3-protecting group-glycerol by introducing R 2 group into 2-position of 1-R 1 -3-protecting group-glycerol; and carrying out the deprotection reaction and the acetylation reaction of 1-R 1 -2-R 2 -3-protecting group-glycerol at the same time. Wherein, R 1 and R 2 are fatty acid groups having 16 to 22 carbon atoms, and are different from each other; and the protecting group is trityl group or trialkylsilyl group.

  揭示了一种高效率和高产率的选择性区域制备甘油衍生物的过程。制备1-R1-2-R2-3-乙酰基甘油衍生物的选择性区域制备过程包括以下步骤：通过在1-R1-甘油的3位引入保护基获得1-R1-3-保护基-甘油；通过在1-R1-3-保护基-甘油的2位引入R2基获得1-R1-2-R2-3-保护基-甘油；同时进行1-R1-2-R2-3-保护基-甘油的去保护反应和乙酰化反应。其中，R1和R2是具有16至22个碳原子的脂肪酸基团，且彼此不同；保护基为三苯基基团或三烷基硅基团。
• Characterization of Pectinatus and Megasphaera Strains by Automated Ribotyping
  作者：Maija-Liisa Suihko、Auli Haikara

  DOI：10.1002/j.2050-0416.2001.tb00089.x

  日期：——

  total of 32 Pectinatus and Megasphaera strains, isolated from spoiled beer or brewery environments and identified by conventional methods, were analysed by the automated RiboPrinter® System. One strain from each ribotype was further subjected to partial 16S rDNA sequencing to confirm the ribotyping results. The restriction enzyme EcoRI was used in ribotyping of Pectinatus strains. Eight strains, identified

  自动化 RiboPrinter® 系统分析了从变质的啤酒或啤酒厂环境中分离并通过常规方法鉴定的总共 32 种 Pectinatus 和 Megasphaera 菌株。每种核糖型的一个菌株进一步进行部分 16S rDNA 测序以确认核糖分型结果。限制酶 EcoRI 用于 Pectinatus 菌株的核糖分型。通过常规测试鉴定为 P. cerevisiiphilus 的八种菌株产生了五种不同的核糖型。三种类型的菌株被认为是 P. cerevisiiphilus 的成员，但两种类型的菌株很可能是 Pectinatus 属内一个新物种的成员。通过常规测试鉴定为 P. frisingenis 的 24 株菌株产生了 9 种不同的核糖型。核糖型之间的相似性相当低，但所有这些菌株显然属于同一物种。用三种限制性酶 EcoRI、Pstl 和 PvuII 分析了 13 种 Megasphaera cerevisiae
• Kraft,R. et al., Journal fur praktische Chemie (Leipzig 1954), 1979, vol. 321, p. 756 - 768
  作者：Kraft,R. et al.

  DOI：——

  日期：——
• WO2007/11150
  申请人：——

  公开号：——

  公开（公告）日：——
• Verkade; van der Lee, Recueil des Travaux Chimiques des Pays-Bas, 1936, vol. 55, p. 267,271
  作者：Verkade、van der Lee

  DOI：——

  日期：——