1,4-bis(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)benzene | 157554-19-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-bis(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)benzene
• 英文别名: 1,4-Bis-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[4-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyphenoxy]oxan-2-yl]methyl acetate
• CAS: 157554-19-3
• 化学式: C₃₄H₄₂O₂₀
• 分子量: 770.695
• InChiKey: SFMNRGNNIJWOLH-CCHDLNLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  54
• 可旋转键数：
  22
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  247
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  1,4-bis(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)benzene 在 甲醇 、 sodium hydride 作用下， 反应 24.0h， 以90%的产率得到1,4-bis(β-D-glucopyranosyl)benzene
  参考文献：
  名称：

  Structure Rationalization and Topology Prediction of Two-Distinct-Component Organic Crystals:  The Role of Volume Fraction and Interface Topology

  摘要：

  We consider here small-length-scale crystal structures with two clearly different molecular components (e.g., hydrophobic and hydrophilic). Using a perspective developed by studies on large-length-scale block copolymers and liquid crystals, we focus on the crystalline interface between the two components. We examine four types of two-component crystals: aromatic ammonium carboxylates, aromatic oligo(ethylene oxides), cyclohexylammonium carboxylates, and ether-thioether compounds. Of the 111 crystal structures found in the Cambridge Structure Database (CSD), 108 adopt one of the five generic topologies found in diblock copolymers: spheres, columns, perforated layers, layers, and bicontinuous structures. As in diblock copolymers, a key factor controlling the interfacial topology is shown to be the volume ratio of the two components. When the volume fraction of one component is less than 30% of the whole, more than five-sixths of the examined crystal structures are of columnar or spherical type. For volume fractions between 40 and 50% more than three-quarters are of lamellar or bicontinuous type. We use this model to predict the topologies of small-length-scale two-component crystals. We predict the crystal topolgies of six new crystal structures: three are predicted to be columnar, and the other three, lamellar or bicontinuous. The crystal structures of these systems were then determined by single-crystal X-ray methods. Five of the structures form in topologies consistent with the predictions: three in columns and two in layers. The remaining one forms as a perforated layer instead of the predicted columnar structure. Such predictive accuracy is consistent with the statistics of the CSD investigation.

  DOI：

  10.1021/ja0115518
• 作为产物：
  描述：

  对苯二酚 、 2,3,4,6-四-O-乙酰基-α-D-吡喃葡萄糖酰氟 在 三氟化硼乙醚 、 四甲基胍 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以74%的产率得到1,4-bis(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)benzene
  参考文献：
  名称：

  Yamaguchi, Masahiko; Horiguchi, Akira; Fukuda, Akira, Journal of the Chemical Society. Perkin transactions I, 1990, # 4, p. 1079 - 1082

  摘要：

  DOI：

文献信息

• Reliable method for the synthesis of aryl β-<scp>D</scp>-glucopyranosides, using boron trifluoride–diethyl ether as catalyst
  作者：Elly Smits、Jan B. F. N. Engberts、Richard M. Kellogg、Henk A. van Doren

  DOI：10.1039/p19960002873

  日期：——

  Stereospecific formation of aryl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosides was achieved by reaction of penta-O-acetyl-β-D-glucose 1 with substituted phenols in the presence of boron trifluoride. Yields of the purified products varied from 52–85%. Benzyl alcohol could also be glucosylated using similar conditions. All products were purified by crystallization from ethanol. The purity and the anomeric

  在三氟化硼的存在下，通过五-O-乙酰基-β - D-葡萄糖1与取代酚的反应，实现了立体异构形成芳基2,3,4,6-四-O-乙酰基-β - D-吡喃葡萄糖苷。纯化产物的产率为52-85％。苯甲醇也可以在类似条件下进行糖基化。通过从乙醇中结晶纯化所有产物。通过1 H和13 C NMR光谱，熔点和旋光度测定产物的纯度和端基异构体构型。
• Synthesis and characterization of a small library of bisglucosides: Influence of the nature of the diol/diphenol used in O-glucosylation
  作者：Stéphane Patry、Mike Robitzer、Jean-Pierre Habas

  DOI：10.1016/j.carres.2020.108217

  日期：2021.2

  completed by MALDI-TOF MS technique. The nucleophilicity of these dihydroxy compounds is identified as being the main factor that governs the reaction characteristics. In particular, the best selectivity is obtained with the use of hydroquinone. Inversely, by-products (oligomers, deacetylated compounds) are observed with the diols defined by higher nucleophilicity despite the choice of stereoselective

  在本文中，通过两个乙酰化葡萄糖单元与二醇（或二酚）的反应研究了不同双糖苷的合成，以开发一个通用的分子平台，用于未来生物基聚合物的发展。最初使用一组五种二醇和一种二酚，以检查它们的化学骨架对反应产率以及所形成物质的性质和比例的影响。使用由 MALDI-TOF MS 技术完成的 1H 和 13C NMR 光谱鉴定反应产物。这些二羟基化合物的亲核性被认为是控制反应特性的主要因素。特别是，使用对苯二酚可获得最佳选择性。相反，副产品（低聚物、
• Oxidatively induced glycosylation starting from hydroquinone glycosides
  作者：Hans Günter Thomas、Jean-Luc Mieusset

  DOI：10.1016/j.tet.2008.03.056

  日期：2008.5

  several glucosides were produced with yields greater than 77% using DDQ in CH2Cl2 as oxidizing agent. For electrolyses, glycosides of trimethylhydroquinone are preferably used because their low oxidation potentials allow the utilization of an undivided cell. The synthesis of the glycosyl donors was achieved with high efficiency by direct coupling of the phenols with peracetylated monosaccharides employing

  作为一类新的糖基供体，对苯二酚糖苷可用于糖基化反应。它们的活化可以电化学或在均相化学条件下进行。常规地，使用CH 2 Cl 2中的DDQ作为氧化剂，生产几种葡糖苷，产率大于77％。对于电解，优选使用三甲基氢醌的糖苷，因为它们的低氧化电位允许利用未分裂的细胞。糖基供体的合成通过使用三氟化硼醚化物作为催化剂，通过使酚与过乙酰化的单糖直接偶联而高效地实现。对苯二酚衍生物的氧化也可用于生成其他稳定的阳离子。
• Clerici, Francesca; Gelmi, Maria Luisa; Mottadelli, Sabrina, Journal of the Chemical Society. Perkin transactions I, 1994, # 8, p. 985 - 988
  作者：Clerici, Francesca、Gelmi, Maria Luisa、Mottadelli, Sabrina

  DOI：——

  日期：——
• Helferich; Reischel, Justus Liebigs Annalen der Chemie, 1938, vol. 533, p. 278,286
  作者：Helferich、Reischel

  DOI：——

  日期：——