1,3,6'-tri-N-benzyloxycarbonyl-kanamycin A-3''-N-succinamide | 1182844-40-1

• 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-kanamycin A-3''-N-succinamide
• CAS: 1182844-40-1
• 化学式: C₄₆H₅₈N₄O₂₀
• 分子量: 986.981
• InChiKey: AMLNOIKMBRJXMX-MBGLTLAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.37
• 重原子数：
  70.0
• 可旋转键数：
  19.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  359.92
• 氢给体数：
  12.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  3,2'-di-N-benzyloxycarbonyl-1,6'-di-N-[N-(2-aminoethyl)aminoformyl]-neamine 、 1,3,6'-tri-N-benzyloxycarbonyl-kanamycin A-3''-N-succinamide 在 吡啶 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 反应 12.0h， 以92%的产率得到N'-[(2S,3R,4S,5S,6R)-3,5-dihydroxy-2-[(1S,2R,3R,4S,6R)-2-hydroxy-4,6-bis[[hydroxy(phenylmethoxy)methylidene]amino]-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[[hydroxy(phenylmethoxy)methylidene]amino]methyl]oxan-2-yl]oxycyclohexyl]oxy-6-(hydroxymethyl)oxan-4-yl]-N-[2-[[[[(2R,3S,4R,5R,6R)-6-[(1R,2R,3S,4R,6S)-4-[[N-[2-[[4-[(2S,3R,4S,5S,6R)-3,5-dihydroxy-2-[(1S,2R,3R,4S,6R)-2-hydroxy-4,6-bis[[hydroxy(phenylmethoxy)methylidene]amino]-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[[hydroxy(phenylmethoxy)methylidene]amino]methyl]oxan-2-yl]oxycyclohexyl]oxy-6-(hydroxymethyl)oxan-4-yl]imino-1,4-dihydroxybutylidene]amino]ethyl]-C-hydroxycarbonimidoyl]amino]-2,3-dihydroxy-6-[[hydroxy(phenylmethoxy)methylidene]amino]cyclohexyl]oxy-3,4-dihydroxy-5-[[hydroxy(phenylmethoxy)methylidene]amino]oxan-2-yl]methylamino]-hydroxymethylidene]amino]ethyl]butanediimidic acid
  参考文献：
  名称：

  Selective deprotection of the Cbz amine protecting group for the facile synthesis of kanamycin A dimers linked at N-3″ position

  摘要：

  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.

  DOI：

  10.1016/j.tet.2009.06.002
• 作为产物：
  描述：

  1,3,6',2''-tetra-N-benzyloxycarbonyl-kanamycin A 在 吡啶 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 16.0h， 生成 1,3,6'-tri-N-benzyloxycarbonyl-kanamycin A-3''-N-succinamide
  参考文献：
  名称：

  Selective deprotection of the Cbz amine protecting group for the facile synthesis of kanamycin A dimers linked at N-3″ position

  摘要：

  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.

  DOI：

  10.1016/j.tet.2009.06.002