N-acetylanilino 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 98911-14-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-acetylanilino 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: N-phenylacetohydroxamic acid 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside；[(2R,3R,4S,5R,6S)-6-(N-acetylanilino)oxy-3,4,5-triacetyloxyoxan-2-yl]methyl acetate
• CAS: 98911-14-9
• 化学式: C₂₂H₂₇NO₁₁
• 分子量: 481.456
• InChiKey: NGCFVPVIESBQPB-BDHVOXNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  144
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N-acetylanilino 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 甲醇 、 Aspergillus niger lipase AS Amano 、 氨 、 水 、 碳酸氢钠 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 乙腈 为溶剂， 反应 3.42h， 生成 N-phenylacetohydroxamic acid 2,4-di-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Complementary and Synergistic Roles in Enzyme-Catalyzed Regioselective and Complete Hydrolytic Deprotection of O-Acetylated β-d-Glucopyranosides of N-Arylacetohydroxamic Acids

  摘要：

  An efficient chemoenzymatic synthesis of beta-D-glucopyranosides of N-arylacetohydroxamic acids 3a-c was achieved by the chemoselective O-deacetylation of 1a-c under mild, neutral conditions, with no accompanying N-deacetylation. Lipase AS Amano from Aspergillus niger (LAS) and carboxylesterase from Streptomyces rochei (CSR) played complementary, synergistic roles in the O-deacetylation of la and its partially O-deacetylated intermediates. An intramolecular O-acetyl migration, which proceeded simultaneously, also accelerated the overall reaction rate. Under weakly acidic conditions at pH 5.0, where the intrarnolecular O-acetyl migration is markedly slower, LAS, CSR, and porcine liver esterase (PLE) exhibited different regioselective O-deacetylation activities. LAS and PLE showed regioselective 3-O-deacetylation and 2-O-deacetylation activity, respectively, for la and its tri-O-acetyl derivatives (4-7). CSR showed marked preferences for 3-O-deacetylation of 2,3,6-tri-O-acetyl intermediate 5 and 4-O-deacetylation of 2,4,6-tri-O-acetyl intermediate 6. In contrast, CSR showed almost no O-deacetylation activity toward the other tri-O-acetyl intermediates 4 and 7, which were efficiently O-deacetylated by LAS in a complementary manner. Using these enzyme-catalyzed regioselective O-deacetylation as well as chemical methods, we could synthesize all 14 partially O-acetylated intermediates (4-17) derived from 1a.

  DOI：

  10.1021/jo202123s
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-1,2-O-<1-(N-acetylanilino-oxy)ethylidene>-α-D-glucopyranose 在 2,6-lutidinium perchlorate 作用下， 以 various solvent(s) 为溶剂， 反应 12.0h， 以59%的产率得到N-acetylanilino 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Yoshioka, Tadao; Uematsu, Takayoshi, Journal of the Chemical Society. Perkin transactions I, 1985, p. 1261 - 1270

  摘要：

  DOI：