5-O-(2'",3'",4'",6'"-tetra-O-acetyl-β-D-galactopyranosyl-(1<*>4)-2",3",6"-tri-O-acetyl-β-D-glucopyranosyl)-1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine | 485810-20-6

• 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: 5-O-(2'",3'",4'",6'"-tetra-O-acetyl-β-D-galactopyranosyl-(1<*>4)-2",3",6"-tri-O-acetyl-β-D-glucopyranosyl)-1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine
• 英文别名: [(2R,3R,4S,5R,6S)-4,5-diacetyloxy-6-[(1R,2R,3S,5R,6S)-3,5-diazido-2-[(2R,3R,4R,5R,6R)-3-azido-6-(azidomethyl)-4,5-bis(phenylmethoxy)oxan-2-yl]oxy-6-phenylmethoxycyclohexyl]oxy-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 485810-20-6
• 化学式: C₅₉H₇₀N₁₂O₂₃
• 分子量: 1315.27
• InChiKey: ZHGSETUHBMFAGY-FLGVPTIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.61
• 重原子数：
  94.0
• 可旋转键数：
  29.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  462.21
• 氢给体数：
  0.0
• 氢受体数：
  27.0

反应信息

• 作为反应物：
  描述：

  5-O-(2'",3'",4'",6'"-tetra-O-acetyl-β-D-galactopyranosyl-(1<*>4)-2",3",6"-tri-O-acetyl-β-D-glucopyranosyl)-1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine 在 sodium hydroxide 、 potassium carbonate 、 三甲基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Pyranmycins, a Novel Class of Aminoglycosides with Improved Acid Stability:  The SAR of d-Pyranoses on Ring III of Pyranmycin

  摘要：

  The synthesis of a novel class of aminoglycosides, pyranmycins, is reported along with the structure activity relationship (SAR) of their antibacterial activity against Escherichia coli. Two pyranmycins show prominent activity (9 muM). Pyranmycins also manifest superior stability in acidic media. The SAR information will lead to the future designs of pyranmycin against drug resistant bacteria.

  DOI：

  10.1021/ol0269042
• 作为产物：
  描述：

  lactose octaacetate 在 4 A molecular sieve 、 乙酸肼 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 5-O-(2'",3'",4'",6'"-tetra-O-acetyl-β-D-galactopyranosyl-(1<*>4)-2",3",6"-tri-O-acetyl-β-D-glucopyranosyl)-1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine
  参考文献：
  名称：

  Pyranmycins, a Novel Class of Aminoglycosides with Improved Acid Stability:  The SAR of d-Pyranoses on Ring III of Pyranmycin

  摘要：

  The synthesis of a novel class of aminoglycosides, pyranmycins, is reported along with the structure activity relationship (SAR) of their antibacterial activity against Escherichia coli. Two pyranmycins show prominent activity (9 muM). Pyranmycins also manifest superior stability in acidic media. The SAR information will lead to the future designs of pyranmycin against drug resistant bacteria.

  DOI：

  10.1021/ol0269042