3-nitro-2-pyridyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside | 250129-85-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-nitro-2-pyridyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
• CAS: 250129-85-2
• 化学式: C₁₉H₂₃N₃O₁₁
• 分子量: 469.405
• InChiKey: WFASLGIFUBWWCT-VDCDIQELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.02
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  182.49
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  3-nitro-2-pyridyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以84.1%的产率得到3-nitro-2-pyridyl N-acetyl-β-D-glucosaminide
  参考文献：
  名称：

  Nitropyridyl glycosides: new glycosyl donors for enzymatic transglycosylation

  摘要：

  New glycosyl donors, 3-nitro-2-pyridyl and 5-nitro-2-pyridyl glycosides, proved to be effective for transglycosylation reaction catalyzed by glycosidases, such as beta-galactosidase, B-glucosidase, and N-acetyl-beta-hexosaminidase. The high solubility in water and the high reactivity of the nitropyridyl glycosides enabled the reactions under high concentrations of the donors and consequently rapid glycosyl transfer to glycosyl accepters. The yields of the transglycosylated products with the nitropyridyl glycosides were much higher than those with conventional p-nitrophenyl glycosides. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01279-4
• 作为产物：
  描述：

  2-羟基-3-硝基吡啶 、 2-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯 在 sodium hydroxide 、 四丁基溴化铵 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 以28.1%的产率得到3-nitro-2-pyridyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Nitropyridyl glycosides: new glycosyl donors for enzymatic transglycosylation

  摘要：

  New glycosyl donors, 3-nitro-2-pyridyl and 5-nitro-2-pyridyl glycosides, proved to be effective for transglycosylation reaction catalyzed by glycosidases, such as beta-galactosidase, B-glucosidase, and N-acetyl-beta-hexosaminidase. The high solubility in water and the high reactivity of the nitropyridyl glycosides enabled the reactions under high concentrations of the donors and consequently rapid glycosyl transfer to glycosyl accepters. The yields of the transglycosylated products with the nitropyridyl glycosides were much higher than those with conventional p-nitrophenyl glycosides. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01279-4