1,3-di-N-benzyloxycarbonyl-6',4':3'',2''-di-N,O-carbonyl-kanamycin A | 69783-64-8

• 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: 1,3-di-N-benzyloxycarbonyl-6',4':3'',2''-di-N,O-carbonyl-kanamycin A
• 英文别名: 1L-O⁴-(3-amino-N,O²-carbonyl-α-D-3-deoxy-glucopyranosyl)-O⁶-(6-amino-N,O⁴-carbonyl-α-D-6-deoxy-glucopyranosyl)-N,N'-bis-benzyloxycarbonyl-2-deoxy-streptamine；N¹,N³-bis-benzyloxycarbonyl-N^{6'_,O4'_;N3''_,O2''}-dicarbonyl-kanamycin-A
• CAS: 69783-64-8
• 化学式: C₃₆H₄₄N₄O₁₇
• 分子量: 804.762
• InChiKey: MRZGTNSDLDFVST-FGLVTWSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.78
• 重原子数：
  57.0
• 可旋转键数：
  11.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  291.39
• 氢给体数：
  9.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  1,3-di-N-benzyloxycarbonyl-6',4':3'',2''-di-N,O-carbonyl-kanamycin A 在 吡啶 、 氨 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以84%的产率得到1,3-di-N-benzyloxycarbonyl-3''-N-(aminoformyl)-6',4'-N,O-carbonyl-kanamycin A
  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：

  1,3,6',2''-tetra-N-benzyloxycarbonyl-kanamycin A 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1,3-di-N-benzyloxycarbonyl-6',4':3'',2''-di-N,O-carbonyl-kanamycin A
  参考文献：
  名称：

  Aminoglycoside antibiotics. 2. N, N-Dialkylkanamycins

  摘要：

  N6',N3''-Dialkyl derivatives of kanamycins A and B were prepared regiospecifically from the parent antibiotics. Although the dimethyl and diethyl derivatives of kanamycin A were inactive in standard antibacterial assays, the dimethyl derivative of kanamycin B showed moderate activity, especially against various strains of Pseudomonas aeruginosa. A method for the selective dimethylation of the 3''-amino group of kanamycin A also was developed.

  DOI：

  10.1021/jm00190a015