<(S)-2-bromo-1-methoxyethyl> 2,3,4,-tri-O-trimethylsilyl-α-D-glucopyranoside | 102088-85-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: <(S)-2-bromo-1-methoxyethyl> 2,3,4,-tri-O-trimethylsilyl-α-D-glucopyranoside
• CAS: 102088-85-7
• 化学式: C₁₈H₄₁BrO₇Si₃
• 分子量: 533.68
• InChiKey: ZCVJSOICTJQUNT-UCIFAOBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  29.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  75.61
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  <(S)-2-bromo-1-methoxyethyl> 2,3,4,-tri-O-trimethylsilyl-α-D-glucopyranoside 在 吡啶 、 水 作用下， 以 甲醇 为溶剂， 反应 17.0h， 生成 <(S)-2-bromo-1-methoxyethyl> 2,3,4-tri-O-acetyl-6-O-mesyl-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：

  <(R)-2-bromo-1-methoxyethyl> α-D-glucopyranoside 在 水 、 溶剂黄146 作用下， 以 吡啶 为溶剂， 反应 150.0h， 生成 <(S)-2-bromo-1-methoxyethyl> 2,3,4,-tri-O-trimethylsilyl-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