(4-methoxycarbonyl-2-nitrophenyl) β-D-galactopyranoside | 931426-23-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-methoxycarbonyl-2-nitrophenyl) β-D-galactopyranoside
• 英文别名: methyl 3-nitro-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoate
• CAS: 931426-23-2
• 化学式: C₁₄H₁₇NO₁₀
• 分子量: 359.29
• InChiKey: AORKARPAMNXVNO-OIRVYTLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  172
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (4-methoxycarbonyl-2-nitrophenyl) β-D-galactopyranoside 在 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 7.0h， 以87%的产率得到(4-carboxy-2-nitrophenyl) β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and evaluation of glycosyl donors with novel leaving groups for transglycosylations employing β-galactosidase from bovine testes

  摘要：

  Novel aryl beta-D-galactopyranosides were synthesized employing phase-transfer catalysis, and assayed as potential galactose donors in the presence of P-galactosidase from bovine testes using pNP-Gal as a reference. The aglycones were represented mainly by nitrophenols containing halogens, hydroxymethyl, aldehyde, carboxyl, ester or amino functions. An unusual intermolecular acetyl migration onto the benzylic alcohol group was observed during galactosylation of hydroxymethylnitrophenols. Pyridyl glycosides were obtained by reaction with the corresponding silver pyridinolates. Glycosides of halo-, hydroxymethyl- or methoxy-carbonyl-nitrophenols as leaving groups gave virtually the same yields of transglycosylation products. A minor increase was achieved with nitrosalicylaldehyde as leaving group, whereas carboxy or amino derivatives gave very low or no yield of the transglycosylation product. Commercially available donors such as resorufinyl and 4-methylumbelliferyl beta-D-galactopyranosides exhibited a lower transglycosylation potential than these novel pNP-Gal derivatives. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.10.014
• 作为产物：
  描述：

  (4-methoxycarbonyl-2-nitrophenyl) 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 氨 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以88%的产率得到(4-methoxycarbonyl-2-nitrophenyl) β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and evaluation of glycosyl donors with novel leaving groups for transglycosylations employing β-galactosidase from bovine testes

  摘要：

  Novel aryl beta-D-galactopyranosides were synthesized employing phase-transfer catalysis, and assayed as potential galactose donors in the presence of P-galactosidase from bovine testes using pNP-Gal as a reference. The aglycones were represented mainly by nitrophenols containing halogens, hydroxymethyl, aldehyde, carboxyl, ester or amino functions. An unusual intermolecular acetyl migration onto the benzylic alcohol group was observed during galactosylation of hydroxymethylnitrophenols. Pyridyl glycosides were obtained by reaction with the corresponding silver pyridinolates. Glycosides of halo-, hydroxymethyl- or methoxy-carbonyl-nitrophenols as leaving groups gave virtually the same yields of transglycosylation products. A minor increase was achieved with nitrosalicylaldehyde as leaving group, whereas carboxy or amino derivatives gave very low or no yield of the transglycosylation product. Commercially available donors such as resorufinyl and 4-methylumbelliferyl beta-D-galactopyranosides exhibited a lower transglycosylation potential than these novel pNP-Gal derivatives. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.10.014

文献信息

• Design, synthesis and enzymatic evaluation of 3- O -substituted aryl β- d -galactopyranosides as inhibitors of Trypanosoma cruzi trans -sialidase
  作者：Bruno L. Silva、José D. S. Filho、Peterson Andrade、Ivone Carvalho、Ricardo J. Alves

  DOI：10.1016/j.bmcl.2014.07.088

  日期：2014.9

  strategies of molecular modification. Ten new aryl galactosides modified at carbon-3 were synthesized employing classical carbohydrate chemistry and dibutyltin oxide method for regioselective 3-O-alkylations and evaluated against TcTS by spectrofluorimetry. The 4-methoxycarbonyl-2-nitrophenyl 3-O-carboxymethyl-β-d-galactopyranoside was the most active compound inhibiting 21% of TcTS enzymatic activity at 1 mM

  克氏锥虫（TcTS）的反唾液酸酶是一种表面酶，可修饰唾液酸覆盖的寄生虫糖萼。这个过程对于人类宿主原生动物生命周期中的粘附和侵袭机制至关重要，这使得TcTS成为药物设计中非常有吸引力的分子靶标。以TcTS底物3'-唾液乳糖为原型，使用分子修饰策略设计了d-半乳糖衍生的TcTS潜在抑制剂。使用经典的碳水化合物化学和二丁基氧化锡方法合成了十个在碳3上修饰的新的芳基半乳糖苷，用于区域选择性3-O-烷基化，并通过光谱荧光法对TcTS进行了评估。4-甲氧羰基-2-硝基苯基3- O-羧甲基-β - d-吡喃半乳糖苷是活性最高的化合物，在1 mM时抑制21％的TcTS酶活性。
• Synthesis and evaluation of glycosyl donors with novel leaving groups for transglycosylations employing β-galactosidase from bovine testes
  作者：Lars Kröger、Joachim Thiem

  DOI：10.1016/j.carres.2006.10.014

  日期：2007.2

  Novel aryl beta-D-galactopyranosides were synthesized employing phase-transfer catalysis, and assayed as potential galactose donors in the presence of P-galactosidase from bovine testes using pNP-Gal as a reference. The aglycones were represented mainly by nitrophenols containing halogens, hydroxymethyl, aldehyde, carboxyl, ester or amino functions. An unusual intermolecular acetyl migration onto the benzylic alcohol group was observed during galactosylation of hydroxymethylnitrophenols. Pyridyl glycosides were obtained by reaction with the corresponding silver pyridinolates. Glycosides of halo-, hydroxymethyl- or methoxy-carbonyl-nitrophenols as leaving groups gave virtually the same yields of transglycosylation products. A minor increase was achieved with nitrosalicylaldehyde as leaving group, whereas carboxy or amino derivatives gave very low or no yield of the transglycosylation product. Commercially available donors such as resorufinyl and 4-methylumbelliferyl beta-D-galactopyranosides exhibited a lower transglycosylation potential than these novel pNP-Gal derivatives. (c) 2006 Elsevier Ltd. All rights reserved.