4-硝基苯基-2-乙酰氨基-3,6-O-二乙酰基-2-脱氧-β-D-吡喃葡萄糖苷 | 61891-87-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-硝基苯基-2-乙酰氨基-3,6-O-二乙酰基-2-脱氧-β-D-吡喃葡萄糖苷
• 中文别名: 4-硝基苯基 2-(乙酰氨基)-2-脱氧-BETA-D-吡喃葡萄糖苷 3,6-二乙酸酯
• 英文名称: 4-nitrophenyl 3,6-di-O-acetyl-2-deoxy-2-(acetamido)-β-D-glucopyranoside
• 英文别名: p-Nitrophenyl 2-Acetamido-2-deoxy-3,6-di-O-acetyl-beta-D-glucopyranoside；[(2R,3S,4R,5R,6S)-5-acetamido-4-acetyloxy-3-hydroxy-6-(4-nitrophenoxy)oxan-2-yl]methyl acetate
• CAS: 61891-87-0
• 化学式: C₁₈H₂₂N₂O₁₀
• 分子量: 426.38
• InChiKey: JUHIIFBVHGQNAI-DUQPFJRNSA-N

物化性质

• 熔点：
  190-192℃ (decomposition)
• 溶解度：
  可溶于氯仿、DMF、DMSO

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  166
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  4-硝基苯基-2-乙酰氨基-3,4,6-O-三乙酰基-2-脱氧-β-D-吡喃葡萄糖苷 在 sodium acetate 作用下， 以 乙腈 为溶剂， 反应 168.0h， 以51%的产率得到p-nitrophenyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Regioselective monohydrolysis of per-O-acetylated-1-substituted-β-glucopyranosides catalyzed by immobilized lipases

  摘要：

  The regioselective monohydrolysis of different peracetylated-beta-glucopyranosides in aqueous media using immobilized preparations of three different lipases-those from Aspergillus niger (ANL), Candida rugose (CRL) and Candida antarctica B (CAL-B)-has been Studied. Three very different immobilization strategies-covalent attachment, anionic exchange and interfacial activation oil a hydrophobic sopport-were employed for each lipase. The role of the immobilization strategy and the effect of the presence of different moieties in the anomeric position of the substrate on the hydrolytic activities, specificities and regioselectivities of the lipases were investigated. For example, the PEI-ANL preparation exhibited 800 times higher activity than the octyl-ANL in the hydrolysis of 2-acetamido-2-deoxy-1-(4-nitrophenyl)-3,4,6-tri-O-acetyl-beta-D-glucopyranoside-producing 4-OH derivative in 18% yield-whereas the octyl-ANL was five times more active than the PEI-ANL in the hydrolysis of 1-(4-nitrophenyl)-2,3,4-tri-O-acetyl-beta-D-xylopyranoside, producing 4-OH monohydroxy product in >99% yield.The octyl-CRL preparation hydrolyzed regioselectively 3,4,6-tri-O-acetyl-glucal in position 6 in 68% yield while the PEI-CRL produced the 3-OH product in 11% yield, although with moderate specificity. The CNBr-CAL-B hydrolyzed specifically and regioselectively the glucal producing the 3-OH product in >99% yield. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.08.099