2-phenylethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-phenylethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: 2-phenylethanol 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside；(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-phenethoxytetrahydro-2H-pyran-3,4,5-triyl triacetate；phenylethyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside；phenethyl-(tetra-O-acetyl-β-D-glucopyranoside)；Phenaethyl-(tetra-O-acetyl-β-D-glucopyranosid)；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(2-phenylethoxy)oxan-2-yl]methyl acetate
• 化学式: C₂₂H₂₈O₁₀
• 分子量: 452.458
• InChiKey: PEYJPADBUUEUGM-QMCAAQAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-phenylethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 sodium methylate 、 叔丁基异氰酸酯 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 2-phenylethanol 6'-O-malonyl β-D-glucopyranoside
  参考文献：
  名称：

  Sensitive and Selective Screening for 6‘-O-Malonylated Glucoconjugates in Plants

  摘要：

  Using synthesized reference compounds a screening for benzyl, 2-phenylethyl, geranyl, citronellyl, and 2,5-dimethyl-4-hydroxy-3(2H)-furanone 6'-O-malonyl beta-D-glucopyranosides in various plant tissues was performed by high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry (HPLC-ESI-MS/MS). The results obtained with fruits (guava; raspberry; strawberry), leaves (green tea; vine), and mountain papaya (Carica pubescens) peel indicate that malonylation of glycoconjugates is a common pathway in plant secondary metabolism.

  DOI：

  10.1021/jf960578l
• 作为产物：
  描述：

  苯基-BETA-葡萄糖吡喃糖苷 在 吡啶 、 phosphate buffer 、 lactase from Kluyveromyces lactis 作用下， 以 硝基苯 为溶剂， 反应 1.0h， 生成 2-phenylethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Mitsuo, Naoki; Takeichi, Hiroshi; Satoh, Toshio, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 3, p. 1183 - 1187

  摘要：

  DOI：

文献信息

• 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。
• Aryl β-d-glucosides from Carica papaya fruit
  作者：Wilfried Schwab、Peter Schreier

  DOI：10.1016/0031-9422(88)80450-3

  日期：1988.1

  Abstract Benzyl β- d -glucoside, 2-phenylethyl β- d -glucoside, 4-hydroxyphenyl-2-ethyl β- d -glucoside and four isomeric malonated benzyl β- d

  摘要 苄基β-d-葡萄糖苷、2-苯乙基β-d-葡萄糖苷、4-羟基苯基-2-乙基β-d-葡萄糖苷和四种异构丙二酸苄基β-d-葡萄糖苷
• Glycosides of 2-phenylethanol and benzyl alcohol in Vitis Vinifera grapes
  作者：P WILLIAMS、C STRAUSS、B WILSON、R MASSYWESTROPP

  DOI：10.1016/0031-9422(83)80040-5

  日期：——

  Abstract β-Rutinosides and 6- O -α- l -arabinofuranosyl-β- d -glucopyranosides of 2-phenylethanol and benzyl alcohol have been found to co-occur with similar disaccharide glycosides of monoterpenes in Vitis vinifera vars. Muscat of Alexandria and Rhine Riesling. β- d -Glucopyranosides of these two alcohols were also identified in the fruit.

  摘要 已发现 2-苯基乙醇和苯甲醇的 β-Rutinosides 和 6-O-α-l-arabinofuranosyl-β-d-吡喃葡萄糖苷与 Vitis vinifera vars 中类似的单萜二糖苷共存。亚历山大马斯喀特和莱茵雷司令。在果实中也鉴定出这两种醇的β-d-吡喃葡萄糖苷。
• Short synthesis of the common trisaccharide core of kankanose and kankanoside isolated from <i>Cistanche tubulosa</i>
  作者：Goutam Guchhait、Anup Kumar Misra

  DOI：10.3762/bjoc.9.80

  日期：——

  A short synthetic approach was developed for the synthesis of a common trisaccharide core found in kankanose, kankanoside F, H₁, H₂, and I isolated from the medicinally active plant Cistanche tubulosa. All glycosylations were carried out under nonmetallic reaction conditions. Yields were very good in all intermediate steps.

  开发了一种简短的合成方法，用于合成从具有药用活性的植物「管花肉苁蓉」中分离出的kankanose、kankanoside F、H₁、H₂和I中常见的三糖核心。所有糖基化反应均在非金属反应条件下进行。所有中间步骤的产率都非常好。
• Preparation of Tea Aroma Precursor Glycosides: An Efficient and Sustainable Approach via Chemical Glycosidation
  作者：Tianlu Li、Tong Li、Youqin Zhang、Richard R. Schmidt、Peng Peng

  DOI：10.1021/acs.jafc.1c07043

  日期：2022.2.23

  addition, the influence of molecular sieves was elucidated. With regard to these findings, the serious problem of the competing orthoester formation side reaction was successfully overcome with low catalyst loading (1 mol %) and the use of 5 Å molecular sieves, leading to the preparation of a variety of tea aroma precursor β-d-glucopyranosides and β-primeverosides on a gram scale in high yields in an economical

  茶香前体甙是植物来源的天然产物，具有很大的经济价值。然而，在过去的几十年中，这些糖苷的制备在很大程度上仍然被忽视。在此，我们报告了一种温和、高效且可持续的化学催化工艺，用于生产茶香气前体糖苷。在研究糖苷化过程中，发现催化剂在有利于不同反应途径的产物形成中起决定性作用；此外，阐明了分子筛的影响。关于这些发现，通过低催化剂负载量（1 mol %）和使用 5 Å 分子筛成功克服了竞争性原酸酯形成副反应的严重问题，从而制备了多种茶香气前体 β- d以经济的方式以克级高产量生产吡喃葡萄糖苷和 β-primeverosides。综上所述，目前的方法具有催化糖苷化的特点，采用无毒、低成本的催化剂，具有良好的绿色性和可持续性，有望实现茶香前体糖苷的工业化生产。