Methyl 2,3,4-tri-O-acetyl-1-O-2,4-dinitrobenzyl-β-D-glucopyranuronate | 202577-46-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Methyl 2,3,4-tri-O-acetyl-1-O-2,4-dinitrobenzyl-β-D-glucopyranuronate
• 英文别名: methyl (2S,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2,4-dinitrophenyl)methoxy]oxane-2-carboxylate
• CAS: 202577-46-6
• 化学式: C₂₀H₂₂N₂O₁₄
• 分子量: 514.4
• InChiKey: OCOBMQAQPRQBHK-KVIJGQROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  36
• 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：
  215
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  Methyl 2,3,4-tri-O-acetyl-1-O-2,4-dinitrobenzyl-β-D-glucopyranuronate 在 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 Potassium 1-O-2,4-dinitrobenzyl-β-D-glucopyranuronate
  参考文献：
  名称：

  Synthesis of Pyridinium Dinitrobenzyl Sulfates and Potassium (Dinitrobenzyl .BETA.-D-Glucopyranosid)Uronates.

  摘要：

  2, 4-二硝基苄醇1a和2, 6-二硝基苄醇1b的主要或假定代谢物，即它们的硫酸酯和葡糖苷酸，是通过1a和1b分别与吡啶硫酸酯和甲基（2, 3, 4-三-O-乙酰基-α-D-吡喃葡萄糖苷酸）溴化物3反应合成的，形成它们的吡啶盐（2a, 2b）和钾盐（6a, 6b）。这些结合物对于研究2, 4-二硝基甲苯（2, 4-DNT）和2, 6-二硝基甲苯（2, 6-DNT）的致癌性至关重要。

  DOI：

  10.1248/cpb.46.145
• 作为产物：
  描述：

  2,4-二硝基苯甲醇 、 乙酰溴-Alpha-D-葡萄糖酮酸甲基酯 在 silver carbonate 作用下， 以 苯 为溶剂， 以10%的产率得到Methyl 2,3,4-tri-O-acetyl-1-O-2,4-dinitrobenzyl-β-D-glucopyranuronate
  参考文献：
  名称：

  Synthesis of Pyridinium Dinitrobenzyl Sulfates and Potassium (Dinitrobenzyl .BETA.-D-Glucopyranosid)Uronates.

  摘要：

  2, 4-二硝基苄醇1a和2, 6-二硝基苄醇1b的主要或假定代谢物，即它们的硫酸酯和葡糖苷酸，是通过1a和1b分别与吡啶硫酸酯和甲基（2, 3, 4-三-O-乙酰基-α-D-吡喃葡萄糖苷酸）溴化物3反应合成的，形成它们的吡啶盐（2a, 2b）和钾盐（6a, 6b）。这些结合物对于研究2, 4-二硝基甲苯（2, 4-DNT）和2, 6-二硝基甲苯（2, 6-DNT）的致癌性至关重要。

  DOI：

  10.1248/cpb.46.145

文献信息

• Further studies on the urinary metabolites of 2,4-dinitrotoluene and 2,6-dinitrotoluene in the male Wistar rat
  作者：M.-A. Mori、M. Shoji、M. Dohrin、T. Kawagoshi、T. Honda、H. Kozuka

  DOI：10.3109/00498259609046690

  日期：1996.1

  1. Conjugates of 2,4-dinitrobenzyl alcohol (2,4-DNB) and 2,6-dinitrobenzyl alcohol (2,6-DNB), which were major urinary metabolites of the male Wistar rat dosed orally with 2,4-dinitrotoluene (2,4-DNT) or 2,6-dinitrotoluene (2,6-DNT), were examined by hplc using potassium 2,4-dinitrobenzyl glucuronide (2,4-DNB-G), potassium 2,6-dinitrobenzyl glucuronide (2,6-DNB-G), pyridinium 2,4-dinitrobenzyl sulphate (2,4-DNB-S), and pyridinium 2,6-dinitrobenzyl sulphate (2,6-DNB-S) as authentic compounds. Other metabolites were also examined by hplc.2. Conjugates detected from urine follow ing administration of 4 -DNT and 2,6-DNT were 2,4-DNB-G and 2,6-DNB-G, which accounted for about 10.7 and 17.4% of the administered dose respectively, No peaks corresponding to pyridinium 2,4-DNB-S and pyridinium 2,6-DNB-S were detected in urine samples.3. 2-Amino-4-nitrobenzoic acid (0.71%), 4-amino-2-nitrobenzoic acid (0.52%) and 4-acetylamino-2-nitrobenzoic acid (3.9%), in addition to known metabolites 4-amino-2-nitrotoluene (0.04%), 2,4-DNB (0.25%), 2,4-dinitrobenzoic acid (6.9%) and 4-acetylamino-2-aminobenzoic acid (3.4%), were detected in ether extracts of urine of rat given 2,4-DNT. 2,6-Dinitrobenzoic acid (0.17%) and two known metabolites, 2-amino-6-nitrotoluene (0.44%) and 2,6-DNB (0.53%), were detected in ether extracts of urine of rat given 2,6-DNT.