2,3,4-tri-O-acetyl-6-deoxy-6-iodo-β-D-glucopyranose | 102088-90-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4-tri-O-acetyl-6-deoxy-6-iodo-β-D-glucopyranose
• 英文别名: 2,3,4-Tri-O-acetyl-6-jod-6-desoxy-β-D-glucopyranose；[(2S,3S,4S,5R,6R)-4,5-diacetyloxy-6-hydroxy-2-(iodomethyl)oxan-3-yl] acetate
• CAS: 102088-90-4
• 化学式: C₁₂H₁₇IO₈
• 分子量: 416.167
• InChiKey: RQBFBJOFMPELQA-RMPHRYRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.07
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  108.36
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-6-deoxy-6-iodo-β-D-glucopyranose 在 sodium azide 、 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 反应 40.0h， 生成 <(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：

  2,3,4-Tri-O-acetyl-6-deoxy-6-iodo-α-D-mannopyranosyliodid 在 水 、 silver carbonate 作用下， 以 丙酮 为溶剂， 反应 0.25h， 以96.7%的产率得到2,3,4-tri-O-acetyl-6-deoxy-6-iodo-β-D-glucopyranose
  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