N-(9-fluorenylmethoxycarbonyl)-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1-3)-L-serine phenacyl ester | 136831-27-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(9-fluorenylmethoxycarbonyl)-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1-3)-L-serine phenacyl ester
• 英文别名: phenacyl (2S)-3-[[(4aR,6S,7R,8R,8aR)-7-acetamido-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate
• CAS: 136831-27-1
• 化学式: C₄₈H₄₆N₂O₁₁
• 分子量: 826.9
• InChiKey: YJVFCORGDAUKFW-CRZFBZNDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  61
• 可旋转键数：
  17
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  157
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N-(9-fluorenylmethoxycarbonyl)-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1-3)-L-serine phenacyl ester 在 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 3.5h， 以88.6%的产率得到N-(9-fluorenylmethoxycarbonyl)-O-(2-acetamido-3-O-benzyl-2-deoxy-α-D-galactopyranosyl)-(1-3)-L-serine phenacyl 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
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranose 在 咪唑 、 二氯二茂锆 、 二乙胺基三氟化硫 、 4 A molecular sieve 、 四丁基氟化铵 、 sodium methylate 、 silver perchlorate 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 58.0h， 生成 N-(9-fluorenylmethoxycarbonyl)-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1-3)-L-serine phenacyl 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