4',5'-dehydro-3',4'-dideoxy-6,3',2'',5'',3''',4'''-hexa-O-methoxycarbonyl-per-N-Cbz-paromomycin | 1284216-88-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4',5'-dehydro-3',4'-dideoxy-6,3',2'',5'',3''',4'''-hexa-O-methoxycarbonyl-per-N-Cbz-paromomycin
• 英文别名: 4',5'-dehydro-3'-deoxy-6,2'',5'',3''',4'''-penta-O-methylcarbonate-per-Cbz-paromomycin
• CAS: 1284216-88-1
• 化学式: C₇₃H₈₃N₅O₃₂
• 分子量: 1542.48
• InChiKey: GKOPZXGBUGQOGW-SRCGFYKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.11
• 重原子数：
  110.0
• 可旋转键数：
  29.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  444.91
• 氢给体数：
  6.0
• 氢受体数：
  32.0

反应信息

• 作为反应物：
  描述：

  4',5'-dehydro-3',4'-dideoxy-6,3',2'',5'',3''',4'''-hexa-O-methoxycarbonyl-per-N-Cbz-paromomycin 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以80%的产率得到4',5'-dehydro-3'-deoxy-per-N-Cbz-paromomycin
  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：

  6'-formyl-4',5'-dehydro-3',4'-dideoxy-6,3',2'',5'',3''',4'''-hexa-O-methoxycarbonyl-per-N-Cbz-paromomycin 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以93%的产率得到4',5'-dehydro-3',4'-dideoxy-6,3',2'',5'',3''',4'''-hexa-O-methoxycarbonyl-per-N-Cbz-paromomycin
  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