{4-(4-amino-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-5-(4-benzyloxycarbonylamino-5-hydroxy-pentanoylamino)-2-[6-(benzyloxycarbonylamino-methyl)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy]-3-hydroxy-cyclohexyl}-carbamic acid benzyl ester | 533923-61-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: {4-(4-amino-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-5-(4-benzyloxycarbonylamino-5-hydroxy-pentanoylamino)-2-[6-(benzyloxycarbonylamino-methyl)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy]-3-hydroxy-cyclohexyl}-carbamic acid benzyl ester
• CAS: 533923-61-4
• 化学式: C₄₇H₆₃N₅O₁₉
• 分子量: 1002.04
• InChiKey: XOOKPIJGQICBLX-ZVHMQOOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.13
• 重原子数：
  71.0
• 可旋转键数：
  20.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  368.87
• 氢给体数：
  13.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  {4-(4-amino-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-5-(4-benzyloxycarbonylamino-5-hydroxy-pentanoylamino)-2-[6-(benzyloxycarbonylamino-methyl)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy]-3-hydroxy-cyclohexyl}-carbamic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 1,4-二氧六环 、 水 、 溶剂黄146 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Probing the functional requirements of the l-haba side-chain of amikacin—synthesis, 16S A-site rRNA binding, and antibacterial activity

  摘要：

  The 1-amino group in amikacin was acylated with a variety of 2-hydroxy aminocarboxylic acids to probe the effect of acylation on ribosomal binding and antibacterial activity. The N-hydroxy urea analogue of amikacin (8a) in which the 2-S-hydroxyl-bearing carbon was replaced by an N-OH group was equally active against S. aureus and E. coli in vitro. The analogous tobramycin variant 9 was more active than amikacin. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01625-3
• 作为产物：
  描述：

  3,6'-bis-N-benzyloxycarbonylkanamycin A 在 ammonium hydroxide 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 为溶剂， 反应 63.0h， 生成 {4-(4-amino-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-5-(4-benzyloxycarbonylamino-5-hydroxy-pentanoylamino)-2-[6-(benzyloxycarbonylamino-methyl)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy]-3-hydroxy-cyclohexyl}-carbamic acid benzyl ester
  参考文献：
  名称：

  Probing the functional requirements of the l-haba side-chain of amikacin—synthesis, 16S A-site rRNA binding, and antibacterial activity

  摘要：

  The 1-amino group in amikacin was acylated with a variety of 2-hydroxy aminocarboxylic acids to probe the effect of acylation on ribosomal binding and antibacterial activity. The N-hydroxy urea analogue of amikacin (8a) in which the 2-S-hydroxyl-bearing carbon was replaced by an N-OH group was equally active against S. aureus and E. coli in vitro. The analogous tobramycin variant 9 was more active than amikacin. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01625-3