(2S,3S,4R)-3,4-di-O-benzyl-1-O-(2,3,4-tri-O-benzyl-6-deoxy-6-(4-benzyltriazol-1-yl)-α-D-galactopyranosyl)-2-hexacosylaminooctadecane-1,3,4-triol | 1415491-05-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3S,4R)-3,4-di-O-benzyl-1-O-(2,3,4-tri-O-benzyl-6-deoxy-6-(4-benzyltriazol-1-yl)-α-D-galactopyranosyl)-2-hexacosylaminooctadecane-1,3,4-triol
• CAS: 1415491-05-2
• 化学式: C₉₄H₁₃₆N₄O₈
• 分子量: 1450.14
• InChiKey: RDQGPOXKOOGFTF-OLGGDWLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  23.5
• 重原子数：
  106.0
• 可旋转键数：
  62.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  124.42
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-3,4-di-O-benzyl-1-O-(2,3,4-tri-O-benzyl-6-deoxy-6-(4-benzyltriazol-1-yl)-α-D-galactopyranosyl)-2-hexacosylaminooctadecane-1,3,4-triol 在 氢气 、 钯 作用下， 以 甲醇 、 氯仿 为溶剂， 以22%的产率得到(2S,3S,4R)-1-O-(6-deoxy-6-(4-benzyltriazol-1-yl)-α-D-galactopyranosyl)-2-hexacosylaminooctadecane-1,3,4-triol
  参考文献：
  名称：

  Synthesis of 6″-triazole-substituted α-GalCer analogues as potent iNKT cell stimulating ligands

  摘要：

  We report the synthesis of a small series of 6 ''-triazol-1-yl-substituted alpha-GalCer analogues by late-stage conversion of the 6 ''-OH to an azide group, copper-catalyzed azide-alkyne cycloaddition and final deprotection. When evaluated for their capacity to induce IL-2 secretion in vitro, all compounds proved equally potent or superior to alpha-GalCer. The S. A. R suggests that the improved antigenic activity is mainly triggered by the triazole functionalization in se. While the introduction of selected substitutuents at C-4 of this heterocyclic ring is tolerated, this generally fails to further improve antigenicity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.063
• 作为产物：
  描述：

  3-苯-1-丙炔 、 (2S,3S,4R)-3,4-di-O-benzyl-1-O-(6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-galactopyranosyl)-2-hexacosylaminooctadecane-1,3,4-triol 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以95%的产率得到(2S,3S,4R)-3,4-di-O-benzyl-1-O-(2,3,4-tri-O-benzyl-6-deoxy-6-(4-benzyltriazol-1-yl)-α-D-galactopyranosyl)-2-hexacosylaminooctadecane-1,3,4-triol
  参考文献：
  名称：

  Synthesis of 6″-triazole-substituted α-GalCer analogues as potent iNKT cell stimulating ligands

  摘要：

  We report the synthesis of a small series of 6 ''-triazol-1-yl-substituted alpha-GalCer analogues by late-stage conversion of the 6 ''-OH to an azide group, copper-catalyzed azide-alkyne cycloaddition and final deprotection. When evaluated for their capacity to induce IL-2 secretion in vitro, all compounds proved equally potent or superior to alpha-GalCer. The S. A. R suggests that the improved antigenic activity is mainly triggered by the triazole functionalization in se. While the introduction of selected substitutuents at C-4 of this heterocyclic ring is tolerated, this generally fails to further improve antigenicity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.063