O--(2-6)-2-acetamido-3-O-benzyl-2-deoxy-α-D-galactopyranosyl>-(1-3)-L-seryl-L-valine benzyl ester | 132183-29-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O--(2-6)-2-acetamido-3-O-benzyl-2-deoxy-α-D-galactopyranosyl>-(1-3)-L-seryl-L-valine benzyl ester
• CAS: 132183-29-0
• 化学式: C₇₆H₈₈N₄O₁₇
• 分子量: 1329.55
• InChiKey: SGESERHNIPIOLQ-UCJZYZQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.11
• 重原子数：
  97.0
• 可旋转键数：
  35.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  269.22
• 氢给体数：
  5.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  O--(2-6)-2-acetamido-3-O-benzyl-2-deoxy-α-D-galactopyranosyl>-(1-3)-L-seryl-L-valine benzyl ester 、 N-(9-fluorenylmethoxycarbonyl)-O--(2-6)-2-acetamido-3-O-benzyl-2-deoxy-α-D-galactopyranosyl>-(1-3)-L-serine 在 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以74%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：

  N-(9-fluorenylmethoxycarbonyl)-O--(2-6)-2-acetamido-3-O-benzyl-2-deoxy-α-D-galactopyranosyl>-(1-3)-L-seryl-L-valine benzyl ester 在 吗啉 作用下， 反应 1.0h， 以95.8%的产率得到O--(2-6)-2-acetamido-3-O-benzyl-2-deoxy-α-D-galactopyranosyl>-(1-3)-L-seryl-L-valine benzyl ester
  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