6'-azido-4',5'-dehydro-3',4'-dideoxy-6,3',2'',5'',3''',4'''-hexa-O-methoxycarbonyl-per-N-Cbz-neomycin | 1284216-89-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 6'-azido-4',5'-dehydro-3',4'-dideoxy-6,3',2'',5'',3''',4'''-hexa-O-methoxycarbonyl-per-N-Cbz-neomycin
• 英文别名: 6'-azido-4',5'-dehydro-3'-deoxy-6,2'',5'',3''',4'''-penta-O-methylcarbonate-per-Cbz-neomycin
• CAS: 1284216-89-2
• 化学式: C₇₃H₈₂N₈O₃₁
• 分子量: 1567.49
• InChiKey: FIPWIDGVPIBSQM-SRCGFYKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.43
• 重原子数：
  112.0
• 可旋转键数：
  30.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  473.44
• 氢给体数：
  5.0
• 氢受体数：
  32.0

反应信息

• 作为反应物：
  描述：

  6'-azido-4',5'-dehydro-3',4'-dideoxy-6,3',2'',5'',3''',4'''-hexa-O-methoxycarbonyl-per-N-Cbz-neomycin 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以488 mg的产率得到6'-azido-4',5'-dehydro-3',4'-dideoxy-per-N-Cbz-neomycin
  参考文献：
  名称：

  Hybrid Aminoglycoside Antibiotics via Tsuji Palladium-Catalyzed Allylic Deoxygenation

  摘要：

  Biosynthetically inspired manipulation of the antibiotic paromomycin led, in six high-yielding steps, to a ring A harboring an alpha,beta-unsaturated 6'-aldehyde and an allylic 3'-methylcarbonate group. Tsuji deoxygenation in the presence of 5 mol % Pd-2(dba)(3) and Bu3P granted access to a novel series of 3',4'-dideoxy-4',5'-dehydro ring A hybrids. The neomycin-sisomicin hybrid exhibited superior in vitro antibacterial activity to the parent compound neomycin.

  DOI：

  10.1021/ol2027703
• 作为产物：
  描述：

  4',5'-dehydro-3',4'-dideoxy-6,3',2'',5'',3''',4'''-hexa-O-methoxycarbonyl-per-N-Cbz-paromomycin 在 二苯基膦叠氮化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以92%的产率得到6'-azido-4',5'-dehydro-3',4'-dideoxy-6,3',2'',5'',3''',4'''-hexa-O-methoxycarbonyl-per-N-Cbz-neomycin
  参考文献：
  名称：

  Hybrid Aminoglycoside Antibiotics via Tsuji Palladium-Catalyzed Allylic Deoxygenation

  摘要：

  Biosynthetically inspired manipulation of the antibiotic paromomycin led, in six high-yielding steps, to a ring A harboring an alpha,beta-unsaturated 6'-aldehyde and an allylic 3'-methylcarbonate group. Tsuji deoxygenation in the presence of 5 mol % Pd-2(dba)(3) and Bu3P granted access to a novel series of 3',4'-dideoxy-4',5'-dehydro ring A hybrids. The neomycin-sisomicin hybrid exhibited superior in vitro antibacterial activity to the parent compound neomycin.

  DOI：

  10.1021/ol2027703

文献信息

• [EN] ANTIBACTERIAL AMINOGLYCOSIDE ANALOGS<br/>[FR] ANALOGUES ANTIBACTÉRIENS D'AMINOGLYCOSIDES
  申请人：ACHAOGEN INC

  公开号：WO2011044498A9

  公开（公告）日：2012-02-09