<(R,S)-1-ethoxyethyl> 2,3,4-tri-O-acetyl-6-deoxy-6-iodo-D-glucopyranoside | 102088-91-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: <(R,S)-1-ethoxyethyl> 2,3,4-tri-O-acetyl-6-deoxy-6-iodo-D-glucopyranoside
• CAS: 102088-91-5；102088-92-6；102088-93-7；102088-94-8
• 化学式: C₁₆H₂₅IO₉
• 分子量: 488.274
• InChiKey: JDOBNOQSSKXCPC-JKMSPKQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.34
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  106.59
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  <(R,S)-1-ethoxyethyl> 2,3,4-tri-O-acetyl-6-deoxy-6-iodo-D-glucopyranoside 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 8.0h， 以57%的产率得到<(R,S)-1-ethoxyethyl> 2,3,4-tri-O-acetyl-6-azido-6-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Comparative stability of 1-alkoxyalkyl α-d-glucosides in the presence of acid or α-d-glucosidase from yeast

  摘要：

  The aminated 1-alkoxyalkyl glycosides [(S)-2-amino-1-methoxyethyl] 6-amino-6-deoxy-alpha-D-glucopyranoside (3) and [(R,S)-1-ethoxyethyl] 6-amino-6-deoxy-alpha-D-glucopyranoside (4) have been synthesised and characterised. These compounds as well as [(R)-2-amino-1-methoxyethyl] alpha-D-glucopyranoside (1) prepared earlier are resistant against alpha-D-glucosidase (maltase, alpha-D-glucoside glucohydrolase, E.C. 3.2.1.20) from yeast, yet undergo hydrolysis under relatively mild acidic conditions. The kinetic parameters of the interaction with alpha-D-glucosidase and with acid were determined. The relative rates of acid hydrolysis of aminated 1-alkoxyalkyl glycosides compared with aminated ordinary glycosides suggest essential differences in the mechanism of acid-catalysed hydrolysis.

  DOI：

  10.1016/s0008-6215(00)90732-8
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-6-deoxy-6-iodo-β-D-glucopyranose 在 水 、 氢溴酸 、 溶剂黄146 、 silver carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 42.25h， 生成 <(R,S)-1-ethoxyethyl> 2,3,4-tri-O-acetyl-6-deoxy-6-iodo-D-glucopyranoside
  参考文献：
  名称：

  Comparative stability of 1-alkoxyalkyl α-d-glucosides in the presence of acid or α-d-glucosidase from yeast

  摘要：

  The aminated 1-alkoxyalkyl glycosides [(S)-2-amino-1-methoxyethyl] 6-amino-6-deoxy-alpha-D-glucopyranoside (3) and [(R,S)-1-ethoxyethyl] 6-amino-6-deoxy-alpha-D-glucopyranoside (4) have been synthesised and characterised. These compounds as well as [(R)-2-amino-1-methoxyethyl] alpha-D-glucopyranoside (1) prepared earlier are resistant against alpha-D-glucosidase (maltase, alpha-D-glucoside glucohydrolase, E.C. 3.2.1.20) from yeast, yet undergo hydrolysis under relatively mild acidic conditions. The kinetic parameters of the interaction with alpha-D-glucosidase and with acid were determined. The relative rates of acid hydrolysis of aminated 1-alkoxyalkyl glycosides compared with aminated ordinary glycosides suggest essential differences in the mechanism of acid-catalysed hydrolysis.

  DOI：

  10.1016/s0008-6215(00)90732-8