(2R,3S,4R,6R)-2-(acetoxymethyl)-5-(hydroxyimino)-6-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate | 80265-00-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: (2R,3S,4R,6R)-2-(acetoxymethyl)-5-(hydroxyimino)-6-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate
• 英文别名: 4-methylumbelliferyl 3,4,6-tri-O-acetyl-2-deoxy-2-oximino-α-D-arabinohexopyranoside
• CAS: 80265-00-5
• 化学式: C₂₂H₂₃NO₁₁
• 分子量: 477.425
• InChiKey: KPVFKIWNLKVNMV-CIQXWFTPSA-N

物化性质

• 沸点：
  656.4±55.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.46
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  160.16
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,6R)-2-(acetoxymethyl)-5-(hydroxyimino)-6-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate 在 吡啶 、 硼烷 作用下， 以 various solvent(s) 为溶剂， 反应 48.08h， 生成 [(2R,3S,4R,5R,6R)-3,4-diacetyloxy-5-amino-6-(4-methyl-2-oxochromen-7-yl)oxyoxan-2-yl]methyl acetate
  参考文献：
  名称：

  4-Methylumbelliferyl 2-acetamido-2-deoxy-α-d-glucopyranoside, a fluorogenic substrate for N-acetyl-α-D-glucos-aminidase

  摘要：

  Condensation of dimeric 3,4,6-tri-O-acetyl-2-deoxy-2-nitroso-alpha-D-glucopyranosyl chloride with 4-methylumbelliferone gave crystalline 4-methylumbelliferyl 3,4,6-tri-O-acetyl-2-deoxy-2-oximino-alpha-D-arabino-hexopyranoside. Acetylation of this adduct, reduction of the resulting crude O-acetyloxime with borane in oxolane, and acetylation gave the 3,4,6-tri-O-acetyl derivative of 4-methylumbelliferyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside (1). A new sensitive assay of N-acetyl-alpha-D-glucosaminidase (EC 3.2.1.50) is made possible by fluorometric measurement of 4-methylumbelliferone liberated by enzymic hydrolysis of glycoside 1. Such assays are illustrated by results obtained with enzyme preparations from pig liver and human-blood serum.

  DOI：

  10.1016/s0008-6215(00)84698-4
• 作为产物：
  描述：

  dimeric 3,4,6-tri-O-acetyl-2-deoxy-2-nitroso-α-D-glucopyranosyl chloride 、 羟甲香豆素 以 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 以18%的产率得到(2R,3S,4R,6R)-2-(acetoxymethyl)-5-(hydroxyimino)-6-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate
  参考文献：
  名称：

  4-Methylumbelliferyl 2-acetamido-2-deoxy-α-d-glucopyranoside, a fluorogenic substrate for N-acetyl-α-D-glucos-aminidase

  摘要：

  Condensation of dimeric 3,4,6-tri-O-acetyl-2-deoxy-2-nitroso-alpha-D-glucopyranosyl chloride with 4-methylumbelliferone gave crystalline 4-methylumbelliferyl 3,4,6-tri-O-acetyl-2-deoxy-2-oximino-alpha-D-arabino-hexopyranoside. Acetylation of this adduct, reduction of the resulting crude O-acetyloxime with borane in oxolane, and acetylation gave the 3,4,6-tri-O-acetyl derivative of 4-methylumbelliferyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside (1). A new sensitive assay of N-acetyl-alpha-D-glucosaminidase (EC 3.2.1.50) is made possible by fluorometric measurement of 4-methylumbelliferone liberated by enzymic hydrolysis of glycoside 1. Such assays are illustrated by results obtained with enzyme preparations from pig liver and human-blood serum.

  DOI：

  10.1016/s0008-6215(00)84698-4