| 132183-31-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 132183-31-4
• 化学式: C₁₅₅H₁₆₉N₇O₃₄
• 分子量: 2674.07
• InChiKey: PVHORLFYJXMYLD-NSAXTZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.09
• 重原子数：
  196.0
• 可旋转键数：
  69.0
• 环数：
  20.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  498.43
• 氢给体数：
  9.0
• 氢受体数：
  34.0

反应信息

• 作为反应物：
  描述：

  在 吗啉 作用下， 反应 1.0h， 以94.6%的产率得到
  参考文献：
  名称：

  Stereoselective total synthesis of glycopeptides bearing the dimeric and trimeric sialosyl-Tn epitope

  摘要：

  The dimeric and trimeric sialosyl-Tn epitopes, [alpha-D-Neup5Ac-(2----6)-alpha-D-GalpNAc-(1----3)-L-Ser]n-L-Val (n = 2 and 3), which represent part of a clustered carbohydrate region of glycophorin A, a human erythrocyte glycoprotein, have been synthesised stereoselectively. 2-Azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-galactopyranosyl fluoride (GalpNAc unit), Fmoc-L-serine phenacyl ester (Ser unit), and benzyl 5-acetamido-4,7,8,9-tetra-O-benzyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-L - gluco-2-nonulopyranosylonate bromide (Neup5Ac unit) were the key intermediates for stereoselective glycosylation. 2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline-promoted elongation of the peptide chain and then hydrogenolysis afforded the title compounds.

  DOI：

  10.1016/0008-6215(92)84163-m
• 作为产物：
  描述：

  在 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 三苯基氢化锡 作用下， 以 苯 为溶剂， 反应 2.0h， 以79.2%的产率得到
  参考文献：
  名称：

  Stereoselective total synthesis of glycopeptides bearing the dimeric and trimeric sialosyl-Tn epitope

  摘要：

  The dimeric and trimeric sialosyl-Tn epitopes, [alpha-D-Neup5Ac-(2----6)-alpha-D-GalpNAc-(1----3)-L-Ser]n-L-Val (n = 2 and 3), which represent part of a clustered carbohydrate region of glycophorin A, a human erythrocyte glycoprotein, have been synthesised stereoselectively. 2-Azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-galactopyranosyl fluoride (GalpNAc unit), Fmoc-L-serine phenacyl ester (Ser unit), and benzyl 5-acetamido-4,7,8,9-tetra-O-benzyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-L - gluco-2-nonulopyranosylonate bromide (Neup5Ac unit) were the key intermediates for stereoselective glycosylation. 2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline-promoted elongation of the peptide chain and then hydrogenolysis afforded the title compounds.

  DOI：

  10.1016/0008-6215(92)84163-m