1-C-(4-azido-2,3,6-tri-O-benzyl-1,4-dideoxy-α-D-galactopyranosyl)propene | 1093187-69-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-C-(4-azido-2,3,6-tri-O-benzyl-1,4-dideoxy-α-D-galactopyranosyl)propene
• CAS: 1093187-69-9
• 化学式: C₃₀H₃₃N₃O₄
• 分子量: 499.61
• InChiKey: CBYSDWFPHWBVAV-ZNOUKXQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  37.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  85.68
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-C-(4-azido-2,3,6-tri-O-benzyl-1,4-dideoxy-α-D-galactopyranosyl)propene 在 air 、 copper dichloride 、 palladium dichloride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 以86%的产率得到1-C-(4-azido-2,3,6-tri-O-benzyl-1,4-dideoxy-α-D-galactopyranosyl)acetone
  参考文献：
  名称：

  Synthesis of iminoalditol analogues of galactofuranosides and their activities against glycosidases

  摘要：

  Iminoalditol analogues of galactofuranosides were synthesized from 1-C-(2'-oxo-propyl)-1,4-dideoxy1,4-imino-D-galactosides and different amines by reductive amination. followed by removal of protecting groups. The activity of these compounds against galactosidases and other glycosidases was investigated. The best inhibitor against beta-galactosidase (bovine liver) is a diastereomeric mixture of an iminoalditol (10h), which contains a hydrophobic hexadecyl aglycon (R=C16H33), whereas no significant inhibitory activity was observed with compounds having a hydrophilic aglycon. Surprisingly, activation of alpha-galactosidase (coffee bean) by 10th was also observed. Because these results were obtained from a mixture of iminoalditols, the inhibition and activation of glycosidases could result from different diastereomers. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.07.013
• 作为产物：
  描述：

  methyl 4-azido-2,3,6-tri-O-benzyl-4-deoxy-α-D-galactopyranoside 、 烯丙基三甲基硅烷 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以70%的产率得到1-C-(4-azido-2,3,6-tri-O-benzyl-1,4-dideoxy-α-D-galactopyranosyl)propene
  参考文献：
  名称：

  Synthesis of iminoalditol analogues of galactofuranosides and their activities against glycosidases

  摘要：

  Iminoalditol analogues of galactofuranosides were synthesized from 1-C-(2'-oxo-propyl)-1,4-dideoxy1,4-imino-D-galactosides and different amines by reductive amination. followed by removal of protecting groups. The activity of these compounds against galactosidases and other glycosidases was investigated. The best inhibitor against beta-galactosidase (bovine liver) is a diastereomeric mixture of an iminoalditol (10h), which contains a hydrophobic hexadecyl aglycon (R=C16H33), whereas no significant inhibitory activity was observed with compounds having a hydrophilic aglycon. Surprisingly, activation of alpha-galactosidase (coffee bean) by 10th was also observed. Because these results were obtained from a mixture of iminoalditols, the inhibition and activation of glycosidases could result from different diastereomers. Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.07.013