4-Cyanophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 187274-83-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Cyanophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: 4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-benzonitrile；4-(Tetra-O-acetyl-β-D-glucopyranosyloxy)-benzonitril；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(4-cyanophenoxy)oxan-2-yl]methyl acetate
• CAS: 187274-83-5
• 化学式: C₂₁H₂₃NO₁₀
• 分子量: 449.414
• InChiKey: YAZPRRKGIXFPAK-YMQHIKHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  147
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4-Cyanophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 生成 p-Cyanophenyl-β-D-glucopyranosid
  参考文献：
  名称：

  Nath; Rydon, Biochemical Journal, 1954, vol. 57, p. 1,2

  摘要：

  DOI：
• 作为产物：
  描述：

  4-羟基苯甲腈 、 β-D-葡萄糖五乙酸酯 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以17%的产率得到4-Cyanophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  以三氟化硼-乙醚为催化剂合成芳基β-D-吡喃葡萄糖苷的可靠方法

  摘要：

  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。

  DOI：

  10.1039/p19960002873

文献信息

• Copper-mediated O-arylation of lactols with aryl boronic acids
  作者：Jing-Jing Sui、De-Cai Xiong、Xin-Shan Ye

  DOI：10.1016/j.cclet.2019.06.014

  日期：2019.8

  Abstract An efficient and novel methodology to access phenolic glycosides has been established by using copper-mediated coupling reaction of aryl boronic acids with hemiacetals. The reaction takes place normally in the presence of Cu(OAc)2 (1.0 equiv.) and pyridine (2.0 equiv.) at 40 °C. This protocol distinguishes itself by wide substrate scope, operational simplicity and giving rise to a myriad of

  摘要：通过铜介导的芳基硼酸与半缩醛的偶联反应，建立了一种有效且新颖的方法来获取酚糖苷。反应通常在40℃下在Cu（OAc）2（1.0当量）和吡啶（2.0当量）存在下进行。该方案通过广泛的底物范围，操作简便性以及以良种至极好的收率产生大量酚类糖苷而独树一帜。
• Application of silver N-heterocyclic carbene complexes in O-glycosidation reactions
  作者：Ian J. Talisman、Vineet Kumar、Jeffrey R. Deschamps、Mark Frisch、Sanjay V. Malhotra

  DOI：10.1016/j.carres.2011.07.025

  日期：2011.11

  We report the efficient O-glycosidation of glycosyl bromides with therapeutically relevant acceptors facilitated by silver N-heterocyclic carbene (Ag-NHC) complexes. A set of four Ag-NHC complexes was synthesized and evaluated as promoters for glycosidation reactions. Two new bis-Ag-NHC complexes derived from ionic liquids 1-benzyl-3-methyl-1H-imidazolium chloride and 1-(2-methoxyethyl)-3-methylimidazolium chloride were found to efficiently promote glycosidation, whereas known mono-Ag complexes of 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride and 1,3-bis(2,6-di-isopropylphenyl)imidazolium chloride failed to facilitate the reaction. The structures of the promoters were established by X-ray crystallography and these complexes were employed in the glycosidation of different glycosyl bromide donors with biologically valuable acceptors, such as estrone, estradiol, and various flavones. The products were obtained in yields considered good to excellent, and all reactions were highly selective for the 13 isomer regardless of neighboring group effects. (C) 2011 Elsevier Ltd. All rights reserved.
• Engineering of glucoside acceptors for the regioselective synthesis of β-(1→3)-disaccharides with glycosynthases
  作者：Zsuzanna Marton、Vinh Tran、Charles Tellier、Michel Dion、Jullien Drone、Claude Rabiller

  DOI：10.1016/j.carres.2008.07.018

  日期：2008.11

  Glycosynthase mutants obtained from Thermotoga maritima were able to catalyze the regioselective synthesis of aryl beta-D-Galp-(1 -> 3)-beta-D-Glcp and aryl beta-D-Glcp-(1 -> 3)-beta-D-Glcp in high yields (up to 90 %) using aryl beta-D-glucosides as acceptors. The need for an aglyconic aryl group was rationalized by molecular modeling calculations, which have emphasized a high stabilizing interaction of this group by stacking with W312 of the enzyme. Unfortunately, the deprotection of the aromatic group of the disaccharides was not possible without partial hydrolysis of the glycosidic bond. The replacement of aryl groups by benzyl ones could offer the opportunity to deprotect the anomeric position under very mild conditions. Assuming that benzyl acceptors could preserve the stabilizing stacking, benzyl beta-D-glucoside firstly assayed as acceptor resulted in both poor yields and poor regioselectivity. Thus, we decided to undertake molecular modeling calculations in order to design which suitable substituted benzyl acceptors could be used. This study resulted in the choice of 2-biphenylmethyl beta-D-glucopyranoside. This choice was validated experimentally, since the corresponding beta-(1 -> 3) disaccharide was obtained in good yields and with a high regioselectivity. At the same time, we have shown that phenyl 1-thio-beta-D-glucopyranoside was also an excellent substrate leading to similar results as those obtained with the O-phenyl analogue. The NBS deprotection of the S-phenyl group afforded the corresponding disaccharide quantitatively. (C) 2008 Elsevier Ltd. All rights reserved.
• 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.
• Solid-Liquid Phase Transfer Catalyzed Novel Glycosylation Reaction of Phenols
  作者：Mitsuya Hongu、Kunio Saito、Kenji Tsujihara

  DOI：10.1080/00397919908086444

  日期：1999.8

  A facile and mild glycosylation reaction in solid-liquid two-phase system (powdered K2CO3 / CHCl3) containing phase transfer catalyst was found to be efficient for preparation of glucosides of 2', 6' -dihydroxyacetophenone (1) and other various substituted phenols.