4-(2,3:4.6-di-O-isopropylidene-mannosyl)-1-(4,5,6-tri-O-benzyl-3-deoxy-β-D-glycero-D-gluco-septanosyl)-1,2,3-triazole | 944478-44-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2,3:4.6-di-O-isopropylidene-mannosyl)-1-(4,5,6-tri-O-benzyl-3-deoxy-β-D-glycero-D-gluco-septanosyl)-1,2,3-triazole
• CAS: 944478-44-8
• 化学式: C₄₁H₅₁N₃O₁₀
• 分子量: 745.87
• InChiKey: JGIACDBABXIDGO-CPHWUVGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.02
• 重原子数：
  54.0
• 可旋转键数：
  13.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  145.01
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  4-(2,3:4.6-di-O-isopropylidene-mannosyl)-1-(4,5,6-tri-O-benzyl-3-deoxy-β-D-glycero-D-gluco-septanosyl)-1,2,3-triazole 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以99%的产率得到4-(2,3-O-isopropylidene-mannopyranosyl)-1-(3-deoxy-β-D-glycero-D-gluco-septanosyl)-1,2,3-triazole
  参考文献：
  名称：

  Synthesis of substituted septanosyl-1,2,3-triazoles

  摘要：

  A carbohydrate-based oxepine, derived from 2-deoxy-D-arabino-hexopyranose, was used to prepare a family of septanosyl-1,2,3-triazoles in four steps. DMDO mediated epoxidation of the oxepine followed by trapping of the intermediate 1,2-anhydroseptanose by sodium azide gave the beta-substituted glycosyl azide. The septanosyl azide was then reacted with a number of alkynes under thermal Huisgen or copper(I) mediated reaction conditions. Hydrogenolysis of benzyl protecting groups gave substituted septanosyl-1,2,3-triazoles. The new septanose-based structures were then evaluated as potential glycosidase inhibitors. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.03.026
• 作为产物：
  描述：

  2,3:4,6-di-O-isopropylidene-D-mannopyranose 在 六甲基磷酰三胺 、 正丁基锂 、 copper diacetate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 3.0h， 生成 4-(2,3:4.6-di-O-isopropylidene-mannosyl)-1-(4,5,6-tri-O-benzyl-3-deoxy-β-D-glycero-D-gluco-septanosyl)-1,2,3-triazole
  参考文献：
  名称：

  Synthesis of substituted septanosyl-1,2,3-triazoles

  摘要：

  A carbohydrate-based oxepine, derived from 2-deoxy-D-arabino-hexopyranose, was used to prepare a family of septanosyl-1,2,3-triazoles in four steps. DMDO mediated epoxidation of the oxepine followed by trapping of the intermediate 1,2-anhydroseptanose by sodium azide gave the beta-substituted glycosyl azide. The septanosyl azide was then reacted with a number of alkynes under thermal Huisgen or copper(I) mediated reaction conditions. Hydrogenolysis of benzyl protecting groups gave substituted septanosyl-1,2,3-triazoles. The new septanose-based structures were then evaluated as potential glycosidase inhibitors. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.03.026