4'-bromophenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside | 2872-68-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4'-bromophenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
• 英文别名: 4-bromophenyl 2,3,4,6-tetra-O-acetyl-β-D-galactoside；4-bromophenyl-tetra-O-acetyl-β-D-galactopyranoside；p-bromophenyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside；p-Bromphenyl-β-D-galactosid-tetraacetat；[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-(4-bromophenoxy)oxan-2-yl]methyl acetate
• CAS: 2872-68-6
• 化学式: C₂₀H₂₃BrO₁₀
• 分子量: 503.301
• InChiKey: YFJHYTOASNBTBZ-LCWAXJCOSA-N

物化性质

• 沸点：
  529.6±50.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 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：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4'-bromophenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 4-bromophenyl β-D-galactopyranoside
  参考文献：
  名称：

  Suzuki偶联反应制备具有联苯间隔基的糖聚合物及其表征

  摘要：

  使用 Suzuku 偶联反应制备在侧链带有糖苷配体的聚 (乙烯基联苯)。研究了糖苷反应物浓度、卤化物种类、糖苷种类和催化剂种类对糖苷配体掺入聚合物中的影响。获得的糖聚合物表现出与糖苷配体对应的蛋白质的特异性结合。此外，由 Suzuki 偶联反应在糖聚合物中形成的联苯间隔物是荧光的，而聚合物前体则不是。

  DOI：

  10.1039/d1ob00617g
• 作为产物：
  描述：

  4-溴苯酚 、 beta-D-半乳糖五乙酸酯 在 磷酸 作用下， 120.0~130.0 ℃ 、4.0 kPa 条件下， 反应 2.0h， 以61%的产率得到4'-bromophenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
  参考文献：
  名称：

  Novik, E. R.; Sokolov, V. M.; Studentsov, E. P., Journal of general chemistry of the USSR, 1986, p. 159 - 165

  摘要：

  DOI：

文献信息

• Phase-Transfer Catalyzed Synthesis of Acetylated Aryl β-D-Glucopyranosides and Aryl β-D-Galactopyranosides
  作者：D. Dess、H. P. Kleine、D. V. Weinberg、R. J. Kaufman、R. S. Sidhu

  DOI：10.1055/s-1981-29631

  日期：——
• Phase-transfer-catalyzed synthesis of 2,3,4,6-tetra-O-acetyl-β-d-galactopyranosides
  作者：Henry P. Kleine、David V. Weinberg、Robert J. Kaufman、Ravinder S. Sidhu

  DOI：10.1016/0008-6215(85)85036-9

  日期：1985.10
• O-Glycosidation reactions promoted by in situ generated silver N-heterocyclic carbenes in ionic liquids
  作者：Ian Jamie Talisman、Vineet Kumar、Jacqueline Razzaghy、Sanjay V. Malhotra

  DOI：10.1016/j.carres.2011.03.007

  日期：2011.5

  We herein report O-glycosidation reactions promoted via silver N-heterocyclic carbene complexes formed in situ in ionic liquids. Seven different room temperature ionic liquids were screened for the glycosidation reaction of 4-nitrophenol with tetra-O-acetyl-alpha-D-galactopyranosyl bromide. Good to excellent yields were obtained using Ag-NHC complexes derived from imidazolium halide salts to promote the glycosidation reaction, whereas yields considered moderate to low were obtained without use of the silver carbene complex. Anion metathesis of the ionic liquids with inexpensive alkylammonium halides also resulted in silver N-heterocyclic carbene formation and subsequent O-glycosidation in the presence of silver carbonate. Effective utility of this methodology has been demonstrated with biologically relevant acceptors (including flavones and steroids) where O-beta-glycoside products were obtained selectively in moderate to good yields. We have also demonstrated that the Ag-NHC complex is a superior promoter to traditionally used silver carbonate for the glycosidation of polyphenolic acceptors. The ionic liquids used in the study could be recycled three times without apparent loss in activity. (C) 2011 Published by Elsevier Ltd.
• Antagonists of the myelin-associated glycoprotein: A new class of tetrasaccharide mimics
  作者：Daniel Schwizer、Heiko Gäthje、Soerge Kelm、Michele Porro、Oliver Schwardt、Beat Ernst

  DOI：10.1016/j.bmc.2006.03.007

  日期：2006.7.15

  The tetrasaccharide substructure 1 of the ganglioside GQ1b alpha shows a remarkable affinity for the myelin-associated glycoprotein (MAG). In the search for structurally simplified and pharmacokinetically improved mimics of 1, biphenyl was identified as a feasible replacement for the core disaccharide Ga1 beta(1-3)Ga1NAc according to saturation transfer difference (STD) NMR and molecular modeling investigations. Using Suzuki coupling, a convergent synthesis of the mimics was achieved. To optimize the yields of the coupling reactions, the catalytic effects of microwave irradiation and conventional heating were compared. The biological evaluation of mimics 3 and 4 was performed in a competitive target-based assay. It was found that the relative inhibitory potency (rIP) of antagonist 3 was clearly enhanced in comparison to the reference trisaccharide 2, despite the former having a much simpler structure. In addition to the improved synthetic feasibility, an increase of the partition coefficient between octanol and water (log P), and therefore a beneficial change in the pharmacokinetic properties of 3 and 4 was achieved. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of carbohydrate functionalised n-propoxy-Calix[4]arenes
  作者：Caroline Félix、Hélène Parrot-Lopez、Vitaly Kalchenko、Anthony W. Coleman

  DOI：10.1016/s0040-4039(98)02136-4

  日期：1998.12

  The Suzuki reaction has been used to couple para-bromophenyl glycosides to boronic acid derivatives of n-propoxy-Calix[4]arene; "a one-pot" methodology eliminates the need to isolate the boronic acids and increases the overall yield. The synthesis provides a new class of carbohydrate containing calixarenes with a deepened cavity. (C) 1998 Elsevier Science Ltd. All rights reserved.