1,2-di-O-oleoyl-3-O-(β-D-glucopyranosyl)-sn-glycerol

• 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: 1,2-di-O-oleoyl-3-O-(β-D-glucopyranosyl)-sn-glycerol
• 英文别名: 1,2-di-O-(cis-9-octadecenoyl)-3-O-(β-D-glucopyranosyl)-sn-glycerol；1,2-O-dioleoyl-3-O-β-D-glucopyranosyl-sn-glycerol；[(2S)-2-[(Z)-octadec-9-enoyl]oxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropyl] (Z)-octadec-9-enoate
• 化学式: C₄₅H₈₂O₁₀
• 分子量: 783.14
• InChiKey: FYKCSQSTKDUTFT-VWBUXCGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.7
• 重原子数：
  55
• 可旋转键数：
  39
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3-O-(β-D-2',3',4',6'-tetra-O-acetyl-glucopyranosyl)-sn-glycerol 在 甲醇 、 ammonium cerium(IV) nitrate 、 sodium methylate 、 sodium hydride 、 4-吡咯烷基吡啶 、 对甲苯磺酸 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 5.0h， 生成 1,2-di-O-oleoyl-3-O-(β-D-glucopyranosyl)-sn-glycerol
  参考文献：
  名称：

  Synthesis and mesogenic properties of glycosyl diacylglycerols

  摘要：

  We synthesised glycosyl diacylglycerols bearing unsaturated or chiral methyl branched fatty acid chains. The thermotropism was measured with polarising microscopy and additionally the lyotropism with the contact preparation method. The synthesised compounds displayed thermotropic S-A (lamellar), cubic and columnar phases and investigation of the lyotropic phase behaviour led to the observation of inverted bicontinuous cubic V-H phases, lamellar L-x phases and normal bicontinuous cubic V-I phases, The phases are discussed with respect to the chemical structures that have been varied systematically to derive structure-property relationships. (C) 2002 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(01)00202-x

文献信息

• Synthesis of dihydrosterculic acid-based monoglucosyl diacylglycerol and its analogues and their biological evaluation
  作者：Vudhgiri Srikanth、R.B.N. Prasad、Y. Poornachandra、V.S. Phani Babu、C. Ganesh Kumar、B. Jagadeesh、Ram Chandra Reddy Jala

  DOI：10.1016/j.ejmech.2015.12.048

  日期：2016.2

  methodology. The β-configuration of the GL1 molecule was unambiguously assigned by NMR studies using 2D-ROESY (NOE) and J-coupling analysis. Dihydrosterculic acid was synthesized using Furukawa's reagent and the selective esterification of dihydrosterculic acid at C-3 position of glycerol was achieved with EDC-HCl at 0 °C. In vitro cytotoxicity of the GL1 molecule and its fatty acid analogues was

  在本研究中，使用三氯乙亚氨酸酯方法合成了β-构型的植物乳杆菌糖脂（GL1）分子及其脂肪酸类似物。使用2D-ROESY（NOE）和J耦合分析的NMR研究明确确定了GL1分子的β-构型。使用Furukawa试剂合成二氢硬脂酸，并在0°C下用EDC-HCl实现甘油在C-3位置的二氢硬脂酸的选择性酯化。评估了GL1分子及其脂肪酸类似物对DU145，A549，SKOV3和MCF7细胞系的体外细胞毒性。在所有合成的分子中，GL1分子和化合物7d表现出中等活性，而该化合物图7b显示了针对所有测试的细胞系的有希望的活性，其IC 50值分别为20.1、18.2、19.1和17.6μM。此外，所有测试的化合物对正常的HUVEC细胞均显示出较弱的细胞毒性。与未处理的细胞相比，当用化合物7b处理时，MCF7细胞显示出较低的溴脱氧尿苷掺入水平，表明化合物7b是高度有效的并且抑制了细胞增殖。此外，这些化合物通过诱导MCF
• RCM-Based Synthesis of a Variety of β-<i>C</i>-Glycosides and Their in Vitro Anti-Solid Tumor Activity
  作者：Maarten H. D. Postema、Jared L. Piper、Russell L. Betts、Frederick A. Valeriote、Halina Pietraszkewicz

  DOI：10.1021/jo040254t

  日期：2005.2.1

  The synthesis of a number of biologically relevant C-glycosides has been carried out through the use of an esterification-ring-closing metathesis (RCM) strategy. The required acid precursors were readily prepared via a number of standard chemical transformations followed by dehydrative coupling of these acids with several olefin alcohols 1 to yield the precursor esters 3 in excellent yield. Methylenation of the esters 3 was followed by RCM and in situ hydroboration-oxidation of the formed glycals to furnish the protected beta-C-glycosides 6 in good overall yield. Several examples were converted to the corresponding C-glycoglycerolipids 17 and subsequently screened against solid-tumor cell lines for in vitro differential cytotoxicity.