m-nitrophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyde | 6118-37-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: m-nitrophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyde
• 英文别名: m-nitrophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside；3-nitrophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside；3-nitrophenol glycoside；1-O-(3′-nitrophenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside；(3-nitro-phenyl)-(tetra-O-acetyl-β-D-glucopyranoside)；(3-Nitro-phenyl)-(tetra-O-acetyl-β-D-glucopyranosid)；m-Nitrophenyl-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosid；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(3-nitrophenoxy)oxan-2-yl]methyl acetate
• CAS: 6118-37-2
• 化学式: C₂₀H₂₃NO₁₂
• 分子量: 469.402
• InChiKey: QIGLGSKMBCHRBZ-OUUBHVDSSA-N

物化性质

• 熔点：
  136-137 °C
• 沸点：
  555.7±50.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  170
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  m-nitrophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyde 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Antibacterial Drug Leads: DNA and Enzyme Multitargeting

  摘要：

  We report the results of an investigation of the activity of a series of amidine and bisamidine compounds against Staphylococcus aureus and Escherichia coli. The most active compounds bound to an AT-rich DNA dodecamer (CGCGAATTCGCG)(2) and using DSC were found to increase the melting transition by up to 24 degrees C. Several compounds also inhibited undecaprenyl diphosphate synthase (UPPS) with IC50 values of 100-500 nM, and we found good correlations (R-2 = 0.89, S. aureus; R-2 = 0.79, E. coli) between experimental and predicted cell growth inhibition by using DNA Delta(Tm) and UPPS IC50 experimental results together with one computed descriptor. We also solved the structures of three bisamidines binding to DNA as well as three UPPS structures. Overall, the results are of general interest in the context of the development of resistance-resistant antibiotics that involve multitargeting.

  DOI：

  10.1021/jm501449u
• 作为产物：
  描述：

  β-D-葡萄糖五乙酸酯 在 sodium hydroxide 、 氢溴酸 、 溶剂黄146 、 丙酮 作用下， 生成 m-nitrophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyde
  参考文献：
  名称：

  AMINO- AND GUANIDINO-PHENYLGLUCOSIDES

  摘要：

  DOI：

  10.1021/jo01150a028

文献信息

• Revisit of the phenol O-glycosylation with glycosyl imidates, BF3·OEt2 is a better catalyst than TMSOTf
  作者：Yali Li、Huaping Mo、Gaoyan Lian、Biao Yu

  DOI：10.1016/j.carres.2012.09.025

  日期：2012.12

  With BF(3)·OEt(2) as the catalyst, the glycosylation of phenols with glycosyl trichloroacetimidates (or N-phenyl trifluoroacetimidates) bearing 2-O-participating groups leads to the desired 1,2-trans-O-glycosides in generally excellent yields without formation of the 1,2-cis-anomers. However, with TMSOTf as the catalyst, the outcomes of the corresponding phenol O-glycosylation are highly dependent

  以BF（3）·OEt（2）为催化剂，苯酚与带有2-O-参与基团的糖基三氯乙酰基亚氨酸盐（或N-苯基三氟乙酰基亚氨酸盐）的糖基化反应通常会产生所需的1,2-反式-O-糖苷极佳的收率，而不会形成1,2-顺式端基异构体。然而，以TMSOTf为催化剂，相应的酚O-糖基化的结果高度依赖于酚的亲核性。苯酚的亲核性越少，生成的1，2-顺式-O-糖苷含量越高，副产物就越多。在所有这些酚O-糖基化反应中，发现1,2-原酸酯是低温（<-70°C）的主要产物，在较高温度下转化为最终产物。BF（3）·OEt（2）是促进1转化的有效催化剂 将2-原酸酯转化为相应的1，2-反式-O-糖苷。然而，在TMSOTf存在下，1,2-原酸酯可被转化为三氟甲磺酸二恶唑鎓和三氟甲磺酸糖基酯，这些中间体可能与糖基氧碳鎓相关物种处于平衡状态，最终形成α/β-O-的最终混合物。苷和副产物。
• Copper-Catalyzed Anomeric O-Arylation of Carbohydrate Derivatives at Room Temperature
  作者：Tristan Verdelet、Sara Benmahdjoub、Belkacem Benmerad、Mouad Alami、Samir Messaoudi

  DOI：10.1021/acs.joc.9b01218

  日期：2019.7.19

  Direct and practical anomeric O-arylation of sugar lactols with substituted arylboronic acids has been established. Using copper catalysis at room temperature under an air atmosphere, the protocol proved to be general, and a variety of aryl O-glycosides have been prepared in good to excellent yields. Furthermore, this approach was extended successfully to unprotected carbohydrates, including α-mannose

  已经建立了糖乳醇与取代的芳基硼酸的直接和实用的异头O-芳基化。在室温，空气气氛下使用铜催化，证明该方案是通用的，并且已经以良好至优异的产率制备了各种芳基O-糖苷。此外，该方法已成功地扩展到未保护的碳水化合物（包括α-甘露糖），并在此证明了碳水化合物和硼酸之间的相互作用如何与铜催化结合以实现选择性的异头O-芳基化。
• Solid-Phase Oligosaccharide and Glycopeptide Synthesis Using Glycosynthases
  作者：Jakob F. Tolborg、Lars Petersen、Knud J. Jensen、Christoph Mayer、David L. Jakeman、R. Antony J. Warren、Stephen G. Withers

  DOI：10.1021/jo0163445

  日期：2002.6.1

  Enzymatic approaches for the preparation of oligosaccharides are interesting alternatives to traditional chemical synthesis, the main advantage being the regio- and stereoselectivity offered without the need for protecting groups. The use of solid-phase techniques offers easy workup procedures and the prospect of automatability. Here, we report the first application of glycosynthases to solid-phase oligosaccharide

  制备低聚糖的酶促方法是传统化学合成的有趣替代方法，其主要优点是无需保护基即可提供区域和立体选择性。固相技术的使用提供了简便的后处理程序，并有望实现自动化。在这里，我们报告通过使用农杆菌sp。的51 kDa丝氨酸和甘氨酸突变体，将糖合酶首次应用于固相寡糖合成。β-葡萄糖苷酶，Abg E358S和E358G。受体通过骨架酰胺连接子（BAL）连接到PEGA树脂，并使用这些突变的酶，以高效率（> 90％）从供体糖α-D-半乳糖氟化物中转移了半乳糖部分，并具有出色的回收率材料。此外，
• Garegg, Per J.; Hultberg, Hans; Ortega, Carmen, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1982, vol. 36, # 8, p. 513 - 514
  作者：Garegg, Per J.、Hultberg, Hans、Ortega, Carmen、Samuelsson, Bertil

  DOI：——

  日期：——
• PRACTICAL β-STEREOSELECTIVE <i>O</i>-GLYCOSYLATION OF PHENOLS WITH PENTA-<i>O</i>-ACETYL-β-<scp>D</scp>-GLUCOPYRANOSE
  作者：Yeon Soo Lee、Eun Suk Rho、Yong Ki Min、Bum Tae Kim、Ki Ho Kim

  DOI：10.1081/car-100106933

  日期：2001.7.31