4-methoxyphenyl 2-(acetylamino)-2-deoxy-β-D-glucopyranoside | 38229-78-6

• 物质功能分类: 医药中间体 - 吡喃类化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl 2-(acetylamino)-2-deoxy-β-D-glucopyranoside
• 英文别名: p-methoxyphenyl 2-acetamido-2-deoxy-β-D-glucopyranoside；p-Methoxy-phenyl-β-acetylglucosaminid；4-methoxyphenyl 2-acetamido-2-deoxy-β-D-glucopyranoside；4'-METHOXYPHENYL-2-ACETAMIDO-2-DEOXY-beta-D-GLUCOPYRANOSIDE；N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-methoxyphenoxy)oxan-3-yl]acetamide
• CAS: 38229-78-6
• 化学式: C₁₅H₂₁NO₇
• 分子量: 327.334
• InChiKey: NGFZIIDJPOHHOD-KJWHEZOQSA-N

物化性质

• 熔点：
  243 °C
• 沸点：
  632.0±55.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  118
• 氢给体数：
  4
• 氢受体数：
  7

安全信息

• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl 2-(acetylamino)-2-deoxy-β-D-glucopyranoside 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 生成 4-methoxyphenyl 2-(acetylamino)-3,4-di-O-benzoyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  分离自白花蛇毒树皮细胞毒性三萜皂苷的三糖的合成

  摘要：

  与从树皮中分离的细胞毒三萜皂苷三糖的化学合成合欢的Procera已经通过一个简明的逐步的糖基化策略来实现从市售起始d木糖，2-乙酰氨基-2-脱氧d葡萄糖和大号-arabinose 。目标三糖与4-甲氧基苯基（MP）糖苷配基一起设计，以通过选择性除去4-甲氧基苯基（MP）基团将转化范围扩展至合适的糖缀合物。一个意外的现象，即阿拉伯糖基残基假定为1 C 4构象，而不是典型的4 C 1形式，被观察到。脱保护可以恢复正常构象。

  DOI：

  10.1002/hlca.201300195
• 作为产物：
  描述：

  4-甲氧基苯基-2-乙酰氨基-3,4,6-三-o-乙酰基-2-脱氧-beta-d-吡喃葡萄糖苷 在 甲醇 、 sodium methylate 作用下， 反应 1.0h， 生成 4-methoxyphenyl 2-(acetylamino)-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  使用多重线性自由能关系探索糖苷水解酶O-GlcNAcase中两种催化策略之间的协同作用

  摘要：

  人类 O-GlcNAcase 在调节丝氨酸和苏氨酸残基与 β-O 连接的 N-乙酰氨基葡萄糖单糖单元 (O-GlcNAc) 的翻译后修饰方面发挥着重要作用。O-GlcNAcase 的机制涉及底物的 2-乙酰氨基基团的亲核参与以取代糖苷连接的离去基团。这种酶对底物结构变化的耐受性使我们能够使用几个系列的底物来表征 O-GlcNAcase 过渡态，以产生多个同时的自由能关系。观察到伴随亲核强度和离去基团能力变化的机制、过渡态和速率决定步骤的变化模式。观察到的机制变化反映了酶通酸和催化亲核试剂所起的作用。重要的是，这些结果说明了酶如何协同利用两种催化模式；许多小分子催化模型都没有的特征。这些研究还表明了氧代碳鎓离子中间体在 O-GlcNAcase 催化的氨基葡萄糖水解中的动力学意义，探索了使用酶过渡态结构的非原子研究可能学到的知识的局限性，并提供了关于保留超家族的一般见解糖苷水解酶作为有效的催化剂。

  DOI：

  10.1021/ja904506u

文献信息

• Scope of the DMC mediated glycosylation of unprotected sugars with phenols in aqueous solution
  作者：Xin Qiu、Antony J. Fairbanks

  DOI：10.1039/d0ob01727b

  日期：——

  sugars in aqueous solution using 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and triethylamine in the presence of para-nitrophenol allows direct stereoselective conversion to the corresponding 1,2-trans para-nitrophenyl glycosides without the need for any protecting groups. The reaction is applicable to sulfated and phosphorylated sugars, but not to ketoses or uronic acids or their derivatives

  在对硝基苯酚存在下，使用 2-氯-1,3-二甲基咪唑啉 (DMC) 和三乙胺在水溶液中活化还原糖，可以直接立体选择性转化为相应的 1,2-反式对硝基苯基糖苷，而无需任何保护基团。该反应适用于硫酸化和磷酸化的糖，但不适用于酮糖或糖醛酸或其衍生物。当应用于其他酚类时，发现产物产率取决于 p K a添加的苯酚，并且该方法不太广泛适用于2-乙酰氨基糖。对于 2-乙酰氨基底物，另一种方法是预先形成糖基恶唑啉，将反应混合物冷冻干燥，然后粗产物与添加的苯酚在极性非质子溶剂系统中与微波辐射反应证明是一种有用的简化.
• Synthesis and conformational analysis of glycomimetic analogs of thiochitobiose
  作者：Anja Fettke、Dirk Peikow、Martin G. Peter、Erich Kleinpeter

  DOI：10.1016/j.tet.2009.03.067

  日期：2009.5

  The synthesis of six analogs of N,N'-diacetylchitobiose is reported, including a novel transglycosylation reaction for the preparation of S-aryl thioglycosides. The conformations of the compounds were studied by a combination of NMR spectroscopy and molecular modeling, using force field calculations. In the case of the S-aryl thioglycosides with exclusively S-glycosidic linkages, dihedral angles of the disaccharidic S-glycosidic bonds, Phi' and Psi' and of the S-arylglycoside bonds, Phi and Psi, were found to be similar, whereas they were different in mixed glycosides and in a thiazoline derivative. An adequate correlation between the calculated H,H-distances of the local minima and the measured NOE contacts was achieved by applying population-weighted averages over participating conformers based on weighted relative energies. (C) 2009 Elsevier Ltd. All rights reserved.
• Thioglycosides Are Efficient Metabolic Decoys of Glycosylation that Reduce Selectin Dependent Leukocyte Adhesion
  作者：Shuen-Shiuan Wang、Xuefeng Gao、Virginia del Solar、Xinheng Yu、Aristotelis Antonopoulos、Alan E. Friedman、Eryn K. Matich、G. Ekin Atilla-Gokcumen、Mehrab Nasirikenari、Joseph T. Lau、Anne Dell、Stuart M. Haslam、Roger A. Laine、Khushi L. Matta、Sriram Neelamegham

  DOI：10.1016/j.chembiol.2018.09.012

  日期：2018.12

  Metabolic decoys are synthetic analogs of naturally occurring biosynthetic acceptors. These compounds divert cellular biosynthetic pathways by acting as artificial substrates that usurp the activity of natural enzymes. While O-linked glycosides are common, they are only partially effective even at millimolar concentrations. In contrast, we report that N-acetylglucosamine (GlcNAc) incorporated into various thioglycosides robustly truncate cell surface N- and O-linked glycan biosynthesis at 10-100 mu M concentrations. The > 10-fold greater inhibition is in part due to the resistance of thioglycosides to hydrolysis by intracellular hexosaminidases. The thioglycosides reduce beta-galactose incorporation into lactosamine chains, cell surface sialyl Lewis-X expression, and leukocyte rolling on selectin substrates including inflamed endothelial cells under fluid shear. Treatment of granulocytes with thioglycosides prior to infusion into mouse inhibited neutrophil homing to sites of acute inflammation and bone marrow by similar to 80%-90%. Overall, thioglycosides represent an easy to synthesize class of efficient metabolic inhibitors or decoys. They reduce N-/O-linked glycan biosynthesis and inflammatory leukocyte accumulation.
• ROY, RENE;TROPPER, FRANCOIS, SYNTH. COMMUN., 20,(1990) N4, C. 2097-2102
  作者：ROY, RENE、TROPPER, FRANCOIS

  DOI：——

  日期：——