1,3,6'-tri-N-benzyloxycarbonyl-3''-N-[N-(2-aminoethyl)aminoformyl]-kanamycin A | 1067641-17-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,6'-tri-N-benzyloxycarbonyl-3''-N-[N-(2-aminoethyl)aminoformyl]-kanamycin A
• 英文别名: benzyl N-[[(2R,3S,4S,5R,6R)-6-[(1R,2R,3S,4R,6S)-3-[(2S,3R,4S,5S,6R)-4-(2-aminoethylcarbamoylamino)-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxy-4,6-bis(phenylmethoxycarbonylamino)cyclohexyl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl]carbamate
• CAS: 1067641-17-1
• 化学式: C₄₅H₆₀N₆O₁₈
• 分子量: 973.001
• InChiKey: XAUDEYDPDCTYSC-CAYLVCQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  69
• 可旋转键数：
  21
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  361
• 氢给体数：
  13
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  1,3,6'-tri-N-benzyloxycarbonyl-3''-N-[N-(2-aminoethyl)aminoformyl]-kanamycin A 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92%的产率得到3''-N-[N-(2-aminoethyl)aminoformyl]-kanamycin A tetrahydrochloride
  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'-tri-N-benzyloxycarbonyl-3'',2''-N,O-carbonyl-kanamycin A 、 乙二胺 在 吡啶 作用下， 以 甲醇 为溶剂， 以87%的产率得到1,3,6'-tri-N-benzyloxycarbonyl-3''-N-[N-(2-aminoethyl)aminoformyl]-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

文献信息

• Selective deprotection of the Cbz amine protecting group for the facile synthesis of kanamycin A dimers linked at N-3″ position
  作者：Gui-Hui Chen、Pan Pan、Ying Chen、Xiang-Bao Meng、Zhong-Jun Li

  DOI：10.1016/j.tet.2009.06.002

  日期：2009.8

  The optimal conditions for the regioselective deprotection of per-N-Cbz-kanamycin A and the reaction mechanism was investigated. We found that the Cbz group at N-3 '' position was selectively deprotected under milder basic conditions and the cyclic carbamate is an intermediate of the deprotection reaction. The selective deprotection of the amine protecting group enable us to synthesize several kanamycin A dimers linked at N-3 '' position in a straightforward way. (C) 2009 Elsevier Ltd. All rights reserved.