4-[5-acetoxy-6-acetoxymethyl-3-acetylamino-4-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-5-(1-benzyloxycarbonyl-2-phenyl-ethoxy)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester | 875801-24-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-[5-acetoxy-6-acetoxymethyl-3-acetylamino-4-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-5-(1-benzyloxycarbonyl-2-phenyl-ethoxy)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester
• CAS: 875801-24-4
• 化学式: C₅₈H₇₇NO₂₄
• 分子量: 1172.24
• InChiKey: VFULWEMJFAWTEM-UACIXPPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  83.0
• 可旋转键数：
  22.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  311.95
• 氢给体数：
  1.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  4-[5-acetoxy-6-acetoxymethyl-3-acetylamino-4-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-5-(1-benzyloxycarbonyl-2-phenyl-ethoxy)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以80%的产率得到
  参考文献：
  名称：

  Ganglioside GM1 mimics: lipophilic substituents improve affinity for cholera toxin

  摘要：

  Ganglioside GM1 mimics including (R)-2-hydroxy-3-cyclohexylpropionic acid or (R)-2-hydroxy-3-phenylpropionic acid as replacements for NeuAc are stronger cholera toxin binders than the parent ligand 2, which includes (R)-2-hydroxy-propionic acid. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.007
• 作为产物：
  描述：

  (S)-3-phenyl-2-trifluoromethanesulfonyloxy-propionic acid benzyl ester 在 三氟甲磺酸 、 二正丁基氧化锡 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 4-[5-acetoxy-6-acetoxymethyl-3-acetylamino-4-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-5-(1-benzyloxycarbonyl-2-phenyl-ethoxy)-cyclohexane-1,2-dicarboxylic acid di-tert-butyl ester
  参考文献：
  名称：

  Ganglioside GM1 mimics: lipophilic substituents improve affinity for cholera toxin

  摘要：

  Ganglioside GM1 mimics including (R)-2-hydroxy-3-cyclohexylpropionic acid or (R)-2-hydroxy-3-phenylpropionic acid as replacements for NeuAc are stronger cholera toxin binders than the parent ligand 2, which includes (R)-2-hydroxy-propionic acid. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.007