3,2'-di-N-benzyloxycarbonyl-1-N-[N-(2-aminoethyl)aminoformyl]-6',4'-N,O-carbonyl-neamine | 1067640-90-7

• 分子结构分类: 有机化合物
• 英文名称: 3,2'-di-N-benzyloxycarbonyl-1-N-[N-(2-aminoethyl)aminoformyl]-6',4'-N,O-carbonyl-neamine
• CAS: 1067640-90-7
• 化学式: C₃₂H₄₂N₆O₁₂
• 分子量: 702.718
• InChiKey: GSSGTQFHVVVJEK-MBLIFSCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.09
• 重原子数：
  50.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  261.29
• 氢给体数：
  9.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  3,2'-di-N-benzyloxycarbonyl-1-N-[N-(2-aminoethyl)aminoformyl]-6',4'-N,O-carbonyl-neamine 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、506.66 kPa 条件下， 反应 8.0h， 以91%的产率得到1-N-[N-(2-aminoethyl)aminoformyl]-6',4'-N,O-carbonyl-neamine trihydrochloride
  参考文献：
  名称：

  Regioselective modification of amino groups in aminoglycosides based on cyclic carbamate formation

  摘要：

  Conditions for regioselective introduction of cyclic carbamate into per-N-Cbz neamine and per-N-Cbz kanamycin A have been found. The position and number of cyclic Carbamate formed in these two aminoglycosides was controllable. On the base of selective cyclic carbamate formation, regioselective modification on N-1, N-6' or both amino groups in neat-nine, and on N-6', N-3 '' or both amino groups in kanamycin A was achieved by ring-opening reaction with amines. A new neamine dimer linked at the N-1 was also synthesized with this method. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.022
• 作为产物：
  描述：

  3,2'-di-N-benzyloxycarbonyl-1,6:6',4'-N,O-carbonyl-neamine 、 乙二胺 在 吡啶 作用下， 以 甲醇 为溶剂， 以84%的产率得到3,2'-di-N-benzyloxycarbonyl-1-N-[N-(2-aminoethyl)aminoformyl]-6',4'-N,O-carbonyl-neamine
  参考文献：
  名称：

  Regioselective modification of amino groups in aminoglycosides based on cyclic carbamate formation

  摘要：

  Conditions for regioselective introduction of cyclic carbamate into per-N-Cbz neamine and per-N-Cbz kanamycin A have been found. The position and number of cyclic Carbamate formed in these two aminoglycosides was controllable. On the base of selective cyclic carbamate formation, regioselective modification on N-1, N-6' or both amino groups in neat-nine, and on N-6', N-3 '' or both amino groups in kanamycin A was achieved by ring-opening reaction with amines. A new neamine dimer linked at the N-1 was also synthesized with this method. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.022