Nα-((fluoren-9-yl)methoxycarbonyl)-Nε-[2-(2',3',4',6'-tetra-O-acetyl-α-D-mannopyranosyloxy)ethyl]-L-lysine | 1171113-23-7

• 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: Nα-((fluoren-9-yl)methoxycarbonyl)-Nε-[2-(2',3',4',6'-tetra-O-acetyl-α-D-mannopyranosyloxy)ethyl]-L-lysine
• 英文别名: (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[2-[(2S,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyethylamino]hexanoic acid
• CAS: 1171113-23-7
• 化学式: C₃₇H₄₆N₂O₁₄
• 分子量: 742.777
• InChiKey: OIUKNDNINOFUKP-ABESABPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  53
• 可旋转键数：
  23
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  211
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  Nα-((fluoren-9-yl)methoxycarbonyl)-Nε-[2-(2',3',4',6'-tetra-O-acetyl-α-D-mannopyranosyloxy)ethyl]-L-lysine 、 2-oxoethyl 2,3,4,6 tetra-O-acetyl-α-D-mannopyranoside 在 三乙酰氧基硼氢化钠 作用下， 以 乙腈 为溶剂， 反应 19.0h， 以238 mg的产率得到Nα-((fluoren-9-yl)methoxycarbonyl)-Nε,Nε-di-[2-(2',3',4',6'-tetra-O-acetyl-α-D-mannopyranosyloxy)ethyl]-L-lysine
  参考文献：
  名称：

  Reductive Amination of the Lysine N ^ε-Amino Group Leads to a Bivalent Glyco-Amino Acid Building Block Suited for SPPS

  摘要：

  Aiming at the synthesis of structurally altered glycopeptides to probe multivalency effects in carbohydrate recognition, a glyco-amino acid building block was prepared, carrying a bivalent carbohydrate branching unit. This new mannosylated lysine derivative was shown to be fully suitable for solid-phase peptide synthesis.

  DOI：

  10.1080/07328300902874795
• 作为产物：
  描述：

  FMOC-赖氨酸 、 2-oxoethyl 2,3,4,6 tetra-O-acetyl-α-D-mannopyranoside 在 三乙酰氧基硼氢化钠 作用下， 以 乙腈 为溶剂， 反应 19.0h， 以76%的产率得到Nα-((fluoren-9-yl)methoxycarbonyl)-Nε-[2-(2',3',4',6'-tetra-O-acetyl-α-D-mannopyranosyloxy)ethyl]-L-lysine
  参考文献：
  名称：

  Reductive Amination of the Lysine N ^ε-Amino Group Leads to a Bivalent Glyco-Amino Acid Building Block Suited for SPPS

  摘要：

  Aiming at the synthesis of structurally altered glycopeptides to probe multivalency effects in carbohydrate recognition, a glyco-amino acid building block was prepared, carrying a bivalent carbohydrate branching unit. This new mannosylated lysine derivative was shown to be fully suitable for solid-phase peptide synthesis.

  DOI：

  10.1080/07328300902874795