3-O-benzyl-1-O-palmitoyl-sn-glycerol | 1487-50-9

• 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: 3-O-benzyl-1-O-palmitoyl-sn-glycerol
• 英文别名: [(2S)-2-Hydroxy-3-phenylmethoxypropyl] hexadecanoate
• CAS: 1487-50-9
• 化学式: C₂₆H₄₄O₄
• 分子量: 420.633
• InChiKey: KTMANQJLYZAYIP-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  30
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2915709000

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-1-O-palmitoyl-sn-glycerol 在 4-二甲氨基吡啶 、 三氯化硼 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 生成 二棕榈酸磷脂酰胆碱
  参考文献：
  名称：

  Synthesis of a Small Library of Mixed-Acid Phospholipids from D-Mannitol as a Homochiral Starting Material.

  摘要：

  描述了一种使用新保护策略合成一系列含有多不饱和脂肪酸的混酸磷脂。具体而言，分别用BCl3和354 nm的光去除的保护基团是苄基和甲基α-(2, 4-二硝基苯基)乙酸。

  DOI：

  10.1248/cpb.47.1659
• 作为产物：
  描述：

  苄基缩水甘油醚 在 chiral salen-based cobalt 四乙基溴化铵 、 水 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 生成 3-O-benzyl-1-O-palmitoyl-sn-glycerol
  参考文献：
  名称：

  Synthesis and Structure of Phosphatidylinositol Dimannoside

  摘要：

  (R)-Tuberculostearic acid (2) was synthesized in seven steps from (S)-citronellol (5). The carbon chain of 2 was assembled by copper-catalyzed cross coupling of (S)-citronellol tosylate (6) and hexylmagnesium bromide; subsequent ozonolysis and reaction with 6-benzyloxyhexylmagnesium bromide furnished alcohol 10. Functional group manipulation afforded (R)-2 in 49% overall yield from 5. DCC coupling of (R)-2 with 3-O-benzyl-1-O-palmitoyl-sn-glycerol (16), followed by hydrogenolytic removal of the benzyl group and treatment with benzyl bis(diisopropyl)phosphoramidite, afforded phosphoramidite 20. Tetrazole-mediated coupling of 20 with PIM1 head group 21 gave 22, and subsequent debenzylation afforded phosphatidylinositol mono-mannoside, PIM1 (23). Similarly, coupling of 20 and 24 and removal of the benzyl protecting groups gave PIM2 (1c). Both 23 and 1c have a clearly defined acylation pattern, which was confirmed by mass spectrometry, with sn-1 palmitoyl and sn-2 tuberculostearoyl groups on the glycerol moiety. Both 23 and 1c were shown to modulate the release of the pro-inflammatory cytokine, IL-12, in a dendritic cell assay.

  DOI：

  10.1021/jo0625599

文献信息

• Synthesis of enantiopure ABC-type triacylglycerols
  作者：Haraldur G. Gudmundsson、Kaisa M. Linderborg、Heikki Kallio、Baoru Yang、Gudmundur G. Haraldsson

  DOI：10.1016/j.tet.2019.130813

  日期：2020.1

  the TAGs possess two different saturated fatty acyl groups located in the sn-1 and sn-2 positions with an unsaturated fatty acyl group in the remaining sn-3 position of the glycerol skeleton, whereas the remaining four possess two different saturated acyl groups in the terminal sn-1 and sn-3 positions with an unsaturated acyl group in the sn-2 position. The former group was synthesised by a six-step

  十二种具有三种不同脂肪酸的ABC型对映体纯结构化三酰甘油（TAGs）的合成是通过从（S）-缩酮开始的六步化学酶促方法进行描述的。八个TAG具有位于sn -1和sn -2位置的两个不同的饱和脂肪酰基，在甘油骨架的其余sn -3位置具有不饱和脂肪酰基，而其余​​四个具有两个不同的饱和酰基在终端SN -1和SN -3位置与所述的不饱和酰基SN-2位置。前一组是通过六步化学酶法合成的，涉及高度区域选择性的固定化念珠菌南极脂肪酶。第二组是通过类似的六步法制备的，该方法需要两个独立的脂肪酶步骤。强烈要求此类对映纯TAG作为对油脂中完整TAG进行对映特异性分析的标准。
• Total synthesis and mass spectrometric analysis of a Mycobacterium tuberculosis phosphatidylglycerol featuring a two-step synthesis of (R)-tuberculostearic acid
  作者：Satvika Burugupalli、Mark B. Richardson、Spencer J. Williams

  DOI：10.1039/c7ob01786c

  日期：——

  We report the total synthesis of (R)-tuberculostearic acid-containing Mycobacterium tuberculosis phosphatidylglycerol (PG). The approach features a two-step synthesis of (R)-tuberculostearic acid, involving an (S)-citronellyl bromide linchpin, and the phosphoramidite-assisted assembly of the full PG structure. Collision-induced dissociation mass spectrometry of two chemically-synthesized PG acyl regioisomers

  我们报告总合成的（R）-结核硬脂酸含结核分枝杆菌磷脂酰甘油（PG）。该方法具有（R）-结核硬脂酸的两步合成方法，其中涉及（S）-香茅基溴化苄基销，以及完整PG结构的亚磷酰胺辅助组装。两种化学合成的PG酰基区域异构体的碰撞诱导解离质谱揭示了诊断产物离子，该离子由羧酸在二级（sn-2）位置的优先丢失而形成。
• Analogues of Glycosphingolipids and Glycerolipids Suitable for Conjugation to Gold- and Amino-Functionalised Surfaces
  作者：Jörgen Ohlsson、Göran Magnusson

  DOI：10.1016/s0040-4020(00)00946-7

  日期：2000.12

  A general synthesis of analogues of natural lipids, (i.e. lactosylceramide, globotriasylceramide, and phosphatidylcholine) where one of the alkyl chains carries a terminal thiol- or carboxyl functionality, is described. The lipids were prepared by N- or O-acylation of sphingosine or monoacylglycerol derivatives. These lipids are suitable for anchoring to gold- or amino-functionalised surfaces, thus

  描述了天然脂类似物（即乳糖基神经酰胺，globoriasyl神经酰胺和磷脂酰胆碱）的类似物的一般合成，其中烷基链之一带有末端硫醇或羧基官能团。通过鞘氨醇或单酰基甘油衍生物的N-或O-酰化制备脂质。这些脂质适用于锚定在金或氨基官能化的表面，从而形成细胞膜的模拟物，用于研究蛋白质与碳水化合物的相互作用。
• H-Phosphonate Synthesis and Biological Evaluation of an Immunomodulatory Phosphoglycolipid from Thermophilic Bacteria
  作者：Chin Heng Gan、Hadhi Wijaya、Lan-Hui Li、Chih-Feng Wei、Yi-Jen Peng、Shih-Hsiung Wu、Kuo-Feng Hua、Yulin Lam

  DOI：10.1021/acs.orglett.0c00487

  日期：2020.4.3

  The synthesis of a library of bacterial phosphoglycolipid, PGL-1, is described. Key features of the synthesis include regioselective esterification of the primary alcohol of the diacylglycerol moiety and an H-phosphonate method to install the phosphate in PGL-1 in comparison with earlier reported procedures. A representative set of PGL-1 analogues was prepared and evaluated for their biological activities

  描述了细菌磷酸糖脂文库PGL-1的合成。与早期报道的方法相比，合成的关键特征包括二酰基甘油部分的伯醇的区域选择性酯化和H-膦酸酯法将磷酸酯安装在PGL-1中。制备了一组代表性的PGL-1类似物，并对其生物学活性进行了评估。结果表明，PGL-1的免疫活性取决于脂肪酸的链长。
• ω-Mercapto analogs of naturally occurring lipids
  作者：Jörgen Ohlsson、Göran Magnusson

  DOI：10.1016/s0040-4039(99)00104-5

  日期：1999.3

  Analogs of natural lipids, where one of the alkyl chains carries a terminal thiol functionality, were prepared by N- or O-acylation of sphingosine or monoacylglycerol derivatives, respectively, thus creating lipid mimics suitable for anchoring to e.g. gold surfaces.

  分别通过鞘氨醇或单酰基甘油衍生物的N-或O-酰化反应制备了其中一个烷基链带有末端硫醇官能度的天然脂质类似物，从而产生了适合锚定于例如金表面的脂质模拟物。