beta-葡糖基甘油2,3,4,6-四乙酸酯 | 157024-67-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 中文名称: beta-葡糖基甘油2,3,4,6-四乙酸酯
• 中文别名: 2-（四乙酰糖苷）甘油
• 英文名称: (β,β'-dihydroxy-isopropyl)-(tetra-O-acetyl-β-D-glucopyranoside)
• 英文别名: (β,β'-Dihydroxy-isopropyl)-(tetra-O-acetyl-β-D-glucopyranosid)；2-(Tetraacetylglucosido)glycerol；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(1,3-dihydroxypropan-2-yloxy)oxan-2-yl]methyl acetate
• CAS: 157024-67-4
• 化学式: C₁₇H₂₆O₁₂
• 分子量: 422.386
• InChiKey: XZWUDSNITUMJJW-NQNKBUKLSA-N

物化性质

• 熔点：
  103 °C
• 沸点：
  527.2±50.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、二氯甲烷、乙醇、乙酸乙酯、甲醇、

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  164
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  beta-葡糖基甘油2,3,4,6-四乙酸酯 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以90%的产率得到1,3-二羟基-2-丙基吡喃己糖苷
  参考文献：
  名称：

  A Simple Synthesis of Glucosyl Glycerols

  摘要：

  Beta-D-glucopyranosides, linked to C-2 or C-3 of the glycerol aglicone moiety, were unambiguously synthesized.

  DOI：

  10.1080/00397919408010167
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 palladium on activated charcoal 氢气 、 碘 、 silver carbonate 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 120.0h， 生成 beta-葡糖基甘油2,3,4,6-四乙酸酯
  参考文献：
  名称：

  Synthesis of Glycosyl Glycerols and Related Glycolipids

  摘要：

  Several isomeric glycosyl glycerols were synthesized. Acetylated allyl glycosides of D-glucose and D-galactose were transformed into 1-O-(glycopyranosyl)-rac-glycerols in a three step procedure via the corresponding 2,3-epoxypropyl glycosides and the peracetylated glycosyl glycerols. Tetra-O-benzyl-D-glucose was glycosylated with 1,3-di-O-benzylglycerol to give the alpha-anomer preferentially. The 2-O-(tetra-O-acetyl-beta-glycopyranosyl)-sn-glycerols and 2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding alpha-derivatives of D-mannose were synthesized by selective glycosylation methods from 1,3-di-O-benzylglycerol and 1,3-O-benzylideneglycerol, respectively, and activated sugar compounds followed by hydrogenolysis. After long chain acylation and selective deacetylation the 1,3-di-O-acyl-2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding a-derivative of D-mannose were synthesized.

  DOI：

  10.1080/07328309808007465

文献信息

• Synthesis of <i>N</i>-oxyamide analogues of protein kinase B (Akt) targeting anionic glycoglycerolipids and their antiproliferative activity on human ovarian carcinoma cells
  作者：Marco Zuccolo、Giulia Orsini、Martina Quaglia、Luca Mirra、Cristina Corno、Nives Carenini、Paola Perego、Diego Colombo

  DOI：10.1039/d3ob00891f

  日期：——

  N-Oxyamides of bioactive anionic glycoglycerolipids based on 2-O-β-D-glucosylglycerol were efficiently prepared. However, the oxidation step of the primary hydroxyl group of the glucose moiety in the presence of the N-oxyamide function appeared to be a difficult task that was nevertheless conveniently achieved for the first time by employing a chemoenzymatic laccase/TEMPO procedure. The obtained N-oxyamides

  有效制备了基于2- O -β- D-葡萄糖基甘油的生物活性阴离子甘油脂的N-草酰胺。然而，在N-草酰胺官能团存在下，葡萄糖部分的伯羟基的氧化步骤似乎是一项艰巨的任务，但首次通过采用化学酶漆酶/TEMPO程序方便地实现了这一任务。与相应的生物活性酯类似，所获得的N-羟基酰胺在无血清培养基中比在完全培养基中表现出更高的对卵巢癌IGROV-1细胞增殖的抑制作用。稳定性和血清结合研究表明，在完全培养基中观察到的化合物活性降低可能主要是由于血清蛋白的结合作用，而不是糖甘油脂酰基链的水解降解。此外，无血清条件下的细胞研究结果表明，N-羟基酰胺基团可以增加甘油糖脂的抗增殖活性，而与阴离子羧基的存在无关。除 IGROV-1 之外的其他细胞系的细胞研究也支持该系列化合物对 Akt 过度激活的肿瘤细胞具有一定程度的选择性。
• Dithiols. Part XVII. S-Benzyl derivatives of 2 : 3-dimercaptopropanol and 1 : 3-dimercaptopropan-2-ol
  作者：N. S. Johary、L. N. Owen

  DOI：10.1039/jr9550001302

  日期：——
• Regio- and diastereoselective lipase-catalyzed preparation of acetylated 2-O-glucosylglycerols
  作者：Diego Colombo、Fiamma Rondietti、Antonio Scala、Ida M. Taino、Pranca Marinone Albini、Lucio Toma

  DOI：10.1016/0957-4166(94)80181-9

  日期：1994.7

  2-O-(beta-D-Glucopyranosyl) glycerol and 2-O-(2',3',4',6'-tetra-O-acetyl-beta-D-glucopyranosyl)glycerol have been submitted to lipase-catalyzed acetylation using Pseudomonas cepacia (LPS) and Candida antarctica (LCA) lipases in organic solvent. The reactions involved the glycerol moiety and were highly diastereoselective: LPS yielded the (2S)-1-O-acetylderivative, while, more interestingly, LCA yielded the (2R)-1-O-acetyl-derivative; in this way the natural compound lilioside A could be obtained. Conversely, lipase-catalyzed hydrolysis of the fully acetylated 1,3-di-O-acetyl-2-O-(2',3',4',6'-tetra-O-acetyl-beta-D-glucopyranosyl)glycerol using LCA furnished the (2S)-1-O-acetyl-derivative showing the same steric preference as the reverse reaction.
• Carter, Chemische Berichte, 1930, vol. 63, p. 1684,1687
  作者：Carter

  DOI：——

  日期：——