(S)-N4-([1-[2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl]-[1,2,3]triazol-4-yl]methyl)-2-(4-phenyl-[1,2,3]triazol-1-yl)-N1-prop-2-ynyl-succinamide | 1189342-40-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-N4-([1-[2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl]-[1,2,3]triazol-4-yl]methyl)-2-(4-phenyl-[1,2,3]triazol-1-yl)-N1-prop-2-ynyl-succinamide
• 英文别名: [(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-[4-[[[(3S)-4-oxo-3-(4-phenyltriazol-1-yl)-4-(prop-2-ynylamino)butanoyl]amino]methyl]triazol-1-yl]oxan-2-yl]methyl acetate
• CAS: 1189342-40-2
• 化学式: C₃₂H₃₇N₉O₁₀
• 分子量: 707.7
• InChiKey: MQOCPSVAIZDLSA-BQEMODBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  51
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  237
• 氢给体数：
  3
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  (2-叠氮基乙基)-苯 、 (S)-N4-([1-[2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl]-[1,2,3]triazol-4-yl]methyl)-2-(4-phenyl-[1,2,3]triazol-1-yl)-N1-prop-2-ynyl-succinamide 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 以117 mg的产率得到(S)-N4-([1-[2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl]-[1,2,3]triazol-4-yl]methyl)-N1-[(1-phenethyl-1H-[1,2,3]triazol-4-yl)methyl]-2-(4-phenyl-[1,2,3]triazol-1-yl)-succinamide
  参考文献：
  名称：

  Click à la carte: robust semi-orthogonal alkyne protecting groups for multiple successive azide/alkyne cycloadditions

  摘要：

  We herein describe an in-depth screening and systematic comparison of five classical silyl alkyne protective groups, to evaluate their potential in the context of multiple successive copper (I)-catalyzed alkyne-azide cycloadditions (CuAAC). We confirm the relative sensitivity of TMS, especially under CuAAC conditions. The relative robustness of its higher analogues, and the discovery of mild silver-catalyzed deprotection conditions selective for TES compared to DPS or TIPS allowed us to design a strategy allowing three successive CuAAC on a single scaffold, as we have illustrated by the synthesis of a tris-triazolo model compound. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.093
• 作为产物：
  描述：

  (S)-N4-([1-[2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl]-[1,2,3]triazol-4-yl]methyl)-2-(4-phenyl-[1,2,3]triazol-1-yl)-N1-(3-triisopropylsilyl-prop-2-ynyl)-succinamide 在 四丁基氟化铵 、 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-N4-([1-[2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl]-[1,2,3]triazol-4-yl]methyl)-2-(4-phenyl-[1,2,3]triazol-1-yl)-N1-prop-2-ynyl-succinamide
  参考文献：
  名称：

  Click à la carte: robust semi-orthogonal alkyne protecting groups for multiple successive azide/alkyne cycloadditions

  摘要：

  We herein describe an in-depth screening and systematic comparison of five classical silyl alkyne protective groups, to evaluate their potential in the context of multiple successive copper (I)-catalyzed alkyne-azide cycloadditions (CuAAC). We confirm the relative sensitivity of TMS, especially under CuAAC conditions. The relative robustness of its higher analogues, and the discovery of mild silver-catalyzed deprotection conditions selective for TES compared to DPS or TIPS allowed us to design a strategy allowing three successive CuAAC on a single scaffold, as we have illustrated by the synthesis of a tris-triazolo model compound. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.093