1-(N-arylamino)oxy-1-deoxy-β-D-glucopyranose | 98911-18-3

• 分子结构分类: 有机化合物 - 苯类化合物 - N-苯基羟胺
• 英文名称: 1-(N-arylamino)oxy-1-deoxy-β-D-glucopyranose
• 英文别名: anilino β-D-glucopyranoside；beta-D-Glucopyranose, 1-deoxy-1-((phenylamino)oxy)-；(2S,3R,4S,5S,6R)-2-anilinooxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 98911-18-3
• 化学式: C₁₂H₁₇NO₆
• 分子量: 271.27
• InChiKey: CTWUVINAVVPLRM-ZIQFBCGOSA-N

物化性质

• 沸点：
  487.7±55.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  111
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(N-arylamino)oxy-1-deoxy-β-D-glucopyranose 在 吡啶 、 porcine liver esterase 、 水 、 碳酸氢钠 、 4-甲氧基三苯基氯甲烷 作用下， 以 1,4-二氧六环 、 乙醇 、 二甲基亚砜 为溶剂， 反应 47.33h， 生成 N-phenylacetohydroxamic acid 4,6-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 在 2,6-lutidinium perchlorate 2,6-二甲基吡啶 、 barium methoxide 作用下， 以 甲醇 、 硝基甲烷 为溶剂， 反应 43.5h， 生成 1-(N-arylamino)oxy-1-deoxy-β-D-glucopyranose
  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：

文献信息

• Yoshioka, Tadao; Uematsu, Takayoshi, Journal of the Chemical Society. Perkin transactions II, 1985, p. 1377 - 1382
  作者：Yoshioka, Tadao、Uematsu, Takayoshi

  DOI：——

  日期：——
• Complementary and Synergistic Roles in Enzyme-Catalyzed Regioselective and Complete Hydrolytic Deprotection of <i>O</i>-Acetylated β-<scp>d</scp>-Glucopyranosides of <i>N</i>-Arylacetohydroxamic Acids
  作者：Akiko Baba、Tadao Yoshioka

  DOI：10.1021/jo202123s

  日期：2012.2.17

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

  DOI：——

  日期：——