邻硝基苯基 2,3,4,6-四-O-乙酰基-beta-D-吡喃半乳糖苷 | 3053-17-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 邻硝基苯基 2,3,4,6-四-O-乙酰基-beta-D-吡喃半乳糖苷
• 中文别名: 邻硝基苯基2,3,4,6-四-O-乙酰基-BETA-D-吡喃半乳糖苷；邻硝基苯基2,3,4,6-四-O-乙酰基-beta-D-吡喃半乳糖苷；邻硝基苯基 2,3,4,6-四-O-乙酰基-BETA-D-吡喃半乳糖苷
• 英文名称: o-nitrophenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
• 英文别名: o-nitrophenyl-2,3,4,6-tetraacetyl-β-D-galactopyranoside；(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate；o-Nitrophenyl-β-D-galactosid-tetraacetat；(2-nitro-phenyl)-(tetra-O-acetyl-β-D-galactopyranoside)；(2-Nitro-phenyl)-(tetra-O-acetyl-β-D-galactopyranosid)；beta-D-Galactopyranoside, 2-nitrophenyl, 2,3,4,6-tetraacetate；[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-(2-nitrophenoxy)oxan-2-yl]methyl acetate
• CAS: 3053-17-6
• 化学式: C₂₀H₂₃NO₁₂
• 分子量: 469.402
• InChiKey: ILJYBOOYGRDODX-LCWAXJCOSA-N

物化性质

• 熔点：
  180-182°C
• 溶解度：
  氯仿（微溶）、乙酸乙酯（微溶）

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

安全信息

• 储存条件：
  -20°C

反应信息

• 作为反应物：
  描述：

  邻硝基苯基 2,3,4,6-四-O-乙酰基-beta-D-吡喃半乳糖苷 在 甲醇 、 sodium methylate 作用下， 生成 尾-D-Galactoside,2-nitrophenyl(9CI)
  参考文献：
  名称：

  Aryl O- and S-galactosides and lactosides as specific inhibitors of human galectins-1 and -3: Role of electrostatic potential at O-3

  摘要：

  Phase transfer catalyzed reaction was used for the high yielding synthesis of aryl 1-thio-beta-D-galacto- and lacto-pyranosides carrying a panel of substituents on the phenyl groups. Best galectin-1 inhibitors were simple p-nitrophenyl thiogalactoside 5a for the monosaccharide and o-nitrophenyl thiolactoside 6f or napthylsulfonyl lactoside 8c, both being 20 times better relative to natural ligands. Relative inhibitory properties as low as 2500 and 40 mu M were observed, respectively. The electronic effects of the lactoside aglycons directly influenced the electrostatic potential at O-3, which was associated with the inhibitory potencies against galectin-1. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.010
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 氢溴酸 、 溶剂黄146 、 silver(l) oxide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 14.0h， 生成 邻硝基苯基 2,3,4,6-四-O-乙酰基-beta-D-吡喃半乳糖苷
  参考文献：
  名称：

  Enhancing cellular sulfane sulfur through β-glycosidase-activated persulfide donors: mechanistic insights and oxidative stress mitigation

  摘要：

  报道了一种新的可渗透细胞的过硫化物和硫化氢供体，可以保护细胞免受氧化应激的影响。

  DOI：

  10.1039/d1cc07162a

文献信息

• Application of Halide Molten Salts as Novel Reaction Media for O-Glycosidic Bond Formation
  作者：Vineet Kumar、Ian Jamie Talisman、Sanjay V. Malhotra

  DOI：10.1002/ejoc.201000188

  日期：——

  we have explored the application of halide molten salts as reaction media for O-glycosidic bond formation under basic conditions and mild heating. Eighteen different room-temperature ionic liquids and molten salts, representing four different classes of cations (i.e. imidazolium, pyridinium, pyrrolidinium and ammonium), were screened in the glycosidation reaction of p-nitrophenol with aceto-bromo-α-D-galactose

  在这项研究中，我们探索了卤化物熔盐作为在碱性条件和温和加热下形成 O-糖苷键的反应介质的应用。在对硝基苯酚与乙酰溴-α-D-半乳糖的糖苷化反应中筛选出十八种不同的室温离子液体和熔融盐，代表四种不同类别的阳离子（即咪唑鎓、吡啶鎓、吡咯烷鎓和铵）。1-丁基-4-甲基咪唑鎓氯化物（BMIM·Cl）得到了最好的结果，并将其应用于其他酚类底物的反应中，产率高达80%。所有反应都对β-端基异构体具有高度选择性，并且熔融盐BMIM·Cl可以很容易地重复使用而不会明显降低活性。
• Sol?Gel Polycondensation of Tetraethyl Orthosilicate (TEOS) in Sugar-Based Porphyrin Organogels: Inorganic Conversion of a Sugar-Directed Porphyrinic Fiber Library through Sol?Gel Transcription Processes
  作者：Shin-ichiro Kawano、Shun-ichi Tamaru、Norifumi Fujita、Seiji Shinkai

  DOI：10.1002/chem.200305042

  日期：2004.1.23

  molecular level, which gives structural variety of the gel fibrils, which can be defined by the sugar library. Inorganic conversion of the organic helical fibrils by a sol-gel transcription process successfully gives the helical-silica structures, which finely inherit the organic morphology. A striking observation is that a unimolecular porphyrin-stacking array is also transcribed into silica fibers when

  在其外围具有单糖基团的加糖卟啉（1 ae）已被合理地设计用于新型胶凝剂。这些化合物中的一些倾向于形成足够稳定的一维聚集体，以显示对DMF-醇混合溶剂的成功胶凝能力。特定柱状上部结构中的聚集模式已通过紫外可见光谱（UV / Vis），圆二色性（CD），扫描电子显微镜（SEM）和透射电子显微镜（TEM）进行了详细评估。从1 ac获得的加糖的卟啉凝胶的所有紫​​外线可见光谱均显示出Soret带吸收，该吸收移向较低波长并显着加宽。这种现象表明，这些卟啉核以H聚集的方式彼此强烈相互作用，它驱动一维卟啉堆叠阵列的产生。来自1 a和1 b的有机凝胶的CD光谱（呈异构体形式）显示出几乎对称的图案，而来自1 c的凝胶给出的图案却完全不同。这意味着凝胶原纤维以右旋或左旋方式缠绕。这反映了胶凝剂特定分子结构中的手性。凝胶纤维的SEM结果与CD谱图非常吻合。1 a中的凝胶原纤维具有左旋螺旋，而1 b中的凝胶原纤维
• WO2020141460A5
  申请人：——

  公开号：WO2020141460A5

  公开（公告）日：2023-01-19
• 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.
• New Compounds. Substituted Salicylaldehydes and Derivatives
  作者：Martin Seidman、Karl Link

  DOI：10.1021/ja01165a601

  日期：1950.9