(2R,3R,4S,5S,6R)-5-acetoxy-2-(((1R,2R,3R,5S)-5-(azidomethyl)-2,3,5-trihydroxycyclohexyl)oxy)-6-((benzoyloxy)methyl)-4-(((2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-3-yl benzoate | 342824-31-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5S,6R)-5-acetoxy-2-(((1R,2R,3R,5S)-5-(azidomethyl)-2,3,5-trihydroxycyclohexyl)oxy)-6-((benzoyloxy)methyl)-4-(((2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-3-yl benzoate
• CAS: 342824-31-1
• 化学式: C₆₃H₆₇N₃O₁₇
• 分子量: 1138.23
• InChiKey: NYBRMJACUZZXDI-ZRQSCBSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.75
• 重原子数：
  83.0
• 可旋转键数：
  25.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  262.19
• 氢给体数：
  3.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5S,6R)-5-acetoxy-2-(((1R,2R,3R,5S)-5-(azidomethyl)-2,3,5-trihydroxycyclohexyl)oxy)-6-((benzoyloxy)methyl)-4-(((2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-3-yl benzoate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以85%的产率得到(1R,2R,4S,6R)-4-Azidomethyl-6-[(2R,3R,4S,5S,6R)-3,5-dihydroxy-6-hydroxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-cyclohexane-1,2,4-triol
  参考文献：
  名称：

  Synthesis of Gal determinant epitopes, their glycomimetic variants, and trimeric clusters—relevance to tumor associated antigens and to discordant xenografts

  摘要：

  The synthesis of Gal alpha1 --> 3Gal-quinic acid pseudo-trisaccharides and their elaboration into trimeric clusters is described. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00195-8
• 作为产物：
  描述：

  ((3aR,5R,7R,7aS)-5,7-dihydroxy-2,2-dimethylhexahydro-1,3-benzodioxol-5-yl)methyl 4-methylbenzenesulfonate 在 sodium azide 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 (2R,3R,4S,5S,6R)-5-acetoxy-2-(((1R,2R,3R,5S)-5-(azidomethyl)-2,3,5-trihydroxycyclohexyl)oxy)-6-((benzoyloxy)methyl)-4-(((2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-3-yl benzoate
  参考文献：
  名称：

  Synthesis of Gal determinant epitopes, their glycomimetic variants, and trimeric clusters—relevance to tumor associated antigens and to discordant xenografts

  摘要：

  The synthesis of Gal alpha1 --> 3Gal-quinic acid pseudo-trisaccharides and their elaboration into trimeric clusters is described. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00195-8