Acetic acid (2S,3S,4R,5S,6S)-4,5-diacetoxy-6-acetoxymethyl-2-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-tetrahydro-pyran-3-yl ester | 477329-92-3

• 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: Acetic acid (2S,3S,4R,5S,6S)-4,5-diacetoxy-6-acetoxymethyl-2-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-tetrahydro-pyran-3-yl ester
• CAS: 477329-92-3
• 化学式: C₄₇H₅₄N₁₂O₁₅
• 分子量: 1027.02
• InChiKey: RVRQODWZTUHKKN-MALYSJTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.07
• 重原子数：
  74.0
• 可旋转键数：
  23.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  364.85
• 氢给体数：
  0.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3S,4R,5S,6S)-4,5-diacetoxy-6-acetoxymethyl-2-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-tetrahydro-pyran-3-yl ester 在 palladium dihydroxide sodium hydroxide 、 氢气 、 potassium carbonate 、 三甲基膦 作用下， 以 四氢呋喃 、 甲醇 、 水 、 溶剂黄146 为溶剂， 反应 31.0h， 生成 (2S,3S,4R,5R,6S)-2-[(1R,2R,3S,5R,6S)-3,5-diamino-2-[(2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
  参考文献：
  名称：

  The Synthesis of l-Aminosugar and the Studies of l-Pyranoses on the Ring III of Pyranmycins

  摘要：

  [GRAPHICS]The synthesis of a novel class of aminoglycoside, pyranmycin, and a convenient method for the preparation of 6-amino-L-idopyranosides were reported. One of the members in the reported pyranmycin families, TC010, has prominent activity against Escherichia coli, Staphylococcus aureus, and Bacillus megaterium. We also discovered that the C-4(1) chair conformation on ring III of pyranmycin is essential for the antibacterial activity.

  DOI：

  10.1021/ol026588r
• 作为产物：
  描述：

  beta-L-葡萄糖五乙酸酯 在 4 A molecular sieve 、 三氟化硼乙醚 、 乙酸肼 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 生成 Acetic acid (2S,3S,4R,5S,6S)-4,5-diacetoxy-6-acetoxymethyl-2-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  The Synthesis of l-Aminosugar and the Studies of l-Pyranoses on the Ring III of Pyranmycins

  摘要：

  [GRAPHICS]The synthesis of a novel class of aminoglycoside, pyranmycin, and a convenient method for the preparation of 6-amino-L-idopyranosides were reported. One of the members in the reported pyranmycin families, TC010, has prominent activity against Escherichia coli, Staphylococcus aureus, and Bacillus megaterium. We also discovered that the C-4(1) chair conformation on ring III of pyranmycin is essential for the antibacterial activity.

  DOI：

  10.1021/ol026588r