2-methoxylbenzyl β-D-glucopyranoside | 1195594-47-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methoxylbenzyl β-D-glucopyranoside
• 英文别名: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(2-methoxyphenyl)methoxy]oxane-3,4,5-triol
• CAS: 1195594-47-8
• 化学式: C₁₄H₂₀O₇
• 分子量: 300.309
• InChiKey: AGSFFHJNZXOOSC-RKQHYHRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  109
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-((2-methoxybenzyl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 甲醇 、 sodium methylate 作用下， 反应 2.0h， 以96%的产率得到2-methoxylbenzyl β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis, Biological Activity of Salidroside and Its Analogues

  摘要：

  红景天苷是从传统中草药红景天中分离得到的一种苯丙素苷类化合物，具有广泛的药理活性。本文通过Koenigs-Knorr方法合成了约18种新颖的红景天苷类似物，并利用3-(4,5-二甲基噻唑-2-基)-2,5-二苯基四唑溴盐（MTT）法评估了这些化合物对PC12细胞的影响。这些新颖化合物在苯环上的取代基或糖基供体方面有所不同。根据数据，苯环3和5位带有甲氧基的(3,5-二甲氧基苯基)甲基β-D-葡萄吡喃糖苷和(3,5-二甲氧基苯基)甲基β-D-半乳吡喃糖苷在浓度分别为300 μmol/L和60 μmol/L时显示出最高的细胞生存力。

  DOI：

  10.1248/cpb.58.1627

文献信息

• Using ionic liquid cosolvents to improve enzymatic synthesis of arylalkyl β-d-glucopyranosides
  作者：Rong-Ling Yang、Ning Li、Min-Hua Zong

  DOI：10.1016/j.molcatb.2011.08.009

  日期：2012.1

  Enzymatic synthesis of various arylalkyl beta-D-glucopyranosides catalyzed by prune (Prunus domestica) seed meal via reverse hydrolysis in the mixture of organic solvent, ionic liquid (IL) and phosphate buffer was described. Among four hydrophilic organic solvents tested, ethylene glycol diacetate (EGDA) was found to be the most suitable for enzymatic synthesis of salidroside, a bioactive compound of commercial interest, from D-glucose and tyrosol. The effects of the nature of ionic liquids and their contents on the enzymatic glucosylation were studied. The addition of a suitable amount of ILs including denaturing ones was favorable to shift the reaction equilibrium toward the synthesis, thus improving the yields. Among the examined ILs, the novel IL [BMIm]I proved to be the best. And this IL was applied as the solvent in biocatalysis for the first time. The yields were found to be enhanced between 0.2-fold and 0.5-fold after the addition of 10% (v/v) [BMIm]I. In 10% (v/v) [BMIm]I-containing system, the desired arylalkyl beta-D-glucopyranosides were synthesized with 15-28% yields, among which salidroside was obtained with a yield of 22%. (C) 2011 Elsevier B.V. All rights reserved.
• Synthesis, Biological Activity of Salidroside and Its Analogues
  作者：Yibing Guo、Yahong Zhao、Cheng Zheng、Ying Meng、Yumin Yang

  DOI：10.1248/cpb.58.1627

  日期：——

  Salidroside is a phenylpropanoid glycoside isolated from Rhodiola rosea L., a traditional Chinese medicinal plant, and has displayed a broad spectrum of pharmacological properties. In this paper, about 18 novel salidroside analogues were prepared through Koenigs–Knorr method, the effects of these compounds over PC12 was assessed with the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method. The novel compounds differ in the substituents attached to the benzene ring or in the glycosyl donor. According to the data, compounds (3,5-dimethoxyphenyl)methyl β-D-glucopyranoside and (3,5-dimethoxyphenyl)methyl β-D-galactopyranoside with methoxy group at 3 and 5-positions of the benzene ring were the most viability at concentration of 300 μmol/l and 60 μmol/l, respectively.

  红景天苷是从传统中草药红景天中分离得到的一种苯丙素苷类化合物，具有广泛的药理活性。本文通过Koenigs-Knorr方法合成了约18种新颖的红景天苷类似物，并利用3-(4,5-二甲基噻唑-2-基)-2,5-二苯基四唑溴盐（MTT）法评估了这些化合物对PC12细胞的影响。这些新颖化合物在苯环上的取代基或糖基供体方面有所不同。根据数据，苯环3和5位带有甲氧基的(3,5-二甲氧基苯基)甲基β-D-葡萄吡喃糖苷和(3,5-二甲氧基苯基)甲基β-D-半乳吡喃糖苷在浓度分别为300 μmol/L和60 μmol/L时显示出最高的细胞生存力。