(2R,3S,4S,5R,6S)-4-hydroxy-2-(((4-methoxyphenyl)diphenylmethoxy)methyl)-6-((N-phenylacetamido)oxy)tetrahydro-2H-pyran-3,5-diyl diacetate | 1376935-10-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2R,3S,4S,5R,6S)-4-hydroxy-2-(((4-methoxyphenyl)diphenylmethoxy)methyl)-6-((N-phenylacetamido)oxy)tetrahydro-2H-pyran-3,5-diyl diacetate
• CAS: 1376935-10-2
• 化学式: C₃₈H₃₉NO₁₀
• 分子量: 669.728
• InChiKey: OEOARSHASTZDSO-ORIAJCIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.94
• 重原子数：
  49.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  130.06
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R,6S)-4-hydroxy-2-(((4-methoxyphenyl)diphenylmethoxy)methyl)-6-((N-phenylacetamido)oxy)tetrahydro-2H-pyran-3,5-diyl diacetate 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 3.0h， 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：

  N-phenylacetohydroxamic acid 3,4,6-tri-O-acetyl-β-D-glucopyranoside 在 吡啶 、 Aspergillus niger lipase AS Amano 、 水 作用下， 以 二甲基亚砜 为溶剂， 反应 39.0h， 生成 (2R,3S,4S,5R,6S)-4-hydroxy-2-(((4-methoxyphenyl)diphenylmethoxy)methyl)-6-((N-phenylacetamido)oxy)tetrahydro-2H-pyran-3,5-diyl diacetate
  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