(2R)-1,2-di-O-benzyl-3-O-(2′,3′,4′,6′-tetra-O-acetyl-β-D-galactopyranosyl)glycerol | 55955-33-4

• 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: (2R)-1,2-di-O-benzyl-3-O-(2′,3′,4′,6′-tetra-O-acetyl-β-D-galactopyranosyl)glycerol
• 英文别名: 1,2-di-O-benzyl-3-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-sn-glycerol；1,2-O-dibenzyl-3-O-(β-D-2',3',4',6'-tetra-O-acetyl-glucopyranosyl)-sn-glycerol；1,2-di-O-benzyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-sn-glycerol
• CAS: 55955-33-4
• 化学式: C₃₁H₃₈O₁₂
• 分子量: 602.636
• InChiKey: DCRUXYFMHOHXAW-USAOHEFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  43.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  142.12
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (2R)-1,2-di-O-benzyl-3-O-(2′,3′,4′,6′-tetra-O-acetyl-β-D-galactopyranosyl)glycerol 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 29.0h， 生成 1,2-O-dilauroyl-3-O-(β-D-2',3',4',6'-tetra-O-acetyl-glucopyranosyl)-sn-glycerol
  参考文献：
  名称：

  Synthesis and anti-herpes simplex viral activity of monoglycosyl diglycerides

  摘要：

  Based on the discovery of antiviral beta-galactosyl diglycerides from Clinacanthus nutans leaves, 19 monoglycosyl diglycerides were synthesized and examined for inhibitory effect on herpes simplex virus types I and 2 (HSV-1, HSV-2). A study of the structure-activity relationships of the synthetic monoglycosyl diglycerides indicated that the fatty acyl moieties were critical for inhibitory action with higher activity displayed as the acyl groups became more olefinic in character. The sugar moiety was also important for anti-HSV action; however, the type of sugar (glucose or galactose) did not affect activity. The stereochemistry at C-2 of the glycerol backbone displayed no significant effect on anti-HSV activity. Among the compounds synthesized, 1,2-O-dilinolenoyl-3-O-beta-D-glucopyranosyl-sn-glycerol showed the highest inhibitory activity against HSV-1 and HSV-2 with IC50 values of 12.5 +/- 0.5 and 18.5 +/- 1.5 mug/ml, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2003.09.008
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 氢溴酸 、 mercury(II) cyanide 、 溶剂黄146 、 mercury dibromide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 22.0h， 生成 (2R)-1,2-di-O-benzyl-3-O-(2′,3′,4′,6′-tetra-O-acetyl-β-D-galactopyranosyl)glycerol
  参考文献：
  名称：

  N-Oxyamide-linked glycoglycerolipid coated AuNPs for receptor-targeting imaging and drug delivery

  摘要：

  我们报道了利用N-醛缩醛键连接的糖基甘油脂包覆的金糖纳米颗粒的构建，用于受体靶向成像和药物输送。

  DOI：

  10.1039/c5cc09749e

文献信息

• Chemoenzymatic synthesis of 1-O-acyl-3-O-(6'-O-acyl-β-D-galactopyranosyl)-sn-glycerol
  作者：Takashi Morimoto、Akito Nagatsu、Nobutoshi Murakami、Jinsaku Sakakibara

  DOI：10.1016/0040-4020(95)00299-n

  日期：1995.6

  Convenient synthesis of 1-O-acyl-3-O-(6'-O-acyl-beta-D-galactopyranosyl)-sn-glycerol was studied. The lipase from Achromobacter sp, catalyzed acylation of 3-O-beta-D-galactopyranosyl-sn-glycerol, which contains two primary hydroxyl functions, proceeded regioselectively to furnish 1-O-acyl-3-O-beta-D-galactopyranosyl-sn-glycerol.
• Synthesis and mesogenic properties of glycosyl diacylglycerols
  作者：H.M von Minden、M Morr、G Milkereit、E Heinz、V Vill

  DOI：10.1016/s0009-3084(01)00202-x

  日期：2002.1

  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.