dibenzyl ((1S,3R,4S,5R,6R)-4-(((2S,3R,4S,5S,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-ureidotetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-6-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(ureidomethyl)tetrahydro-2H-pyran-2-yl)oxy)cyclohexane-1,3-diyl)dicarbamate | 1067641-33-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dibenzyl ((1S,3R,4S,5R,6R)-4-(((2S,3R,4S,5S,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-ureidotetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-6-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(ureidomethyl)tetrahydro-2H-pyran-2-yl)oxy)cyclohexane-1,3-diyl)dicarbamate
• CAS: 1067641-33-1
• 化学式: C₃₆H₅₀N₆O₁₇
• 分子量: 838.823
• InChiKey: GPPOOQWTQVXTIC-SUMSFFDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.94
• 重原子数：
  59.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  365.43
• 氢给体数：
  13.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  dibenzyl ((1S,3R,4S,5R,6R)-4-(((2S,3R,4S,5S,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-ureidotetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-6-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(ureidomethyl)tetrahydro-2H-pyran-2-yl)oxy)cyclohexane-1,3-diyl)dicarbamate 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97%的产率得到
  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-di-N-benzyloxycarbonyl-6',4':3'',4''-di-N,O-carbonyl-kanamycin A 在 吡啶 、 氨 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以92%的产率得到dibenzyl ((1S,3R,4S,5R,6R)-4-(((2S,3R,4S,5S,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-ureidotetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-6-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(ureidomethyl)tetrahydro-2H-pyran-2-yl)oxy)cyclohexane-1,3-diyl)dicarbamate
  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