5-O-(4-azido-4,6-dideoxy-β-D-glucopyranosyl)-6-O-allyl-3',4'-di-O-benzyl-1-N-[(S)-2-benzyloxy-4-(benzyloxycarbonylamino)butanoyl]-3,2',6'-triazidoneamine | 959982-92-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-O-(4-azido-4,6-dideoxy-β-D-glucopyranosyl)-6-O-allyl-3',4'-di-O-benzyl-1-N-[(S)-2-benzyloxy-4-(benzyloxycarbonylamino)butanoyl]-3,2',6'-triazidoneamine
• CAS: 959982-92-4
• 化学式: C₅₄H₆₄N₁₄O₁₃
• 分子量: 1117.19
• InChiKey: HTYAGQKVVLGFPY-GFNXJRHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.83
• 重原子数：
  81.0
• 可旋转键数：
  28.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  376.77
• 氢给体数：
  4.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  5-O-(4-azido-4,6-dideoxy-β-D-glucopyranosyl)-6-O-allyl-3',4'-di-O-benzyl-1-N-[(S)-2-benzyloxy-4-(benzyloxycarbonylamino)butanoyl]-3,2',6'-triazidoneamine 在 臭氧 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 3.02h， 以71%的产率得到5-O-(4-azido-4,6-dideoxy-β-D-glucopyranosyl)-6-O-(2-hydroxyethyl)-3',4'-di-O-benzyl-1-N-[(S)-2-benzyloxy-4-(benzyloxycarbonylamino)butanoyl]-3,2',6'-triazidoneamine
  参考文献：
  名称：

  Synthesis and antibacterial activity of pyranmycin derivatives with N-1 and O-6 modifications

  摘要：

  Continuing from our ongoing effort in modifying aminoglycoside antibiotics with the goal of counteracting drug resistant bacteria, we have further derivatized pyranmycin, a neomycin class aminoglycoside antibiotic, with modifications at O-6 and N-1 positions. The revealed SAR results demonstrated that the antibacterial activity of pyranmycin can be modulated by different acylic substituents at O-6. Among these results, the 6-O-aminoethyl derivative, JT050, showed effective activity against resistant strain Escherichia coli (pTZ19U-3) and E. coli (pSF815), which provides insight into further structural modi. cations. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.08.059
• 作为产物：
  描述：

  在 lithium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 以380 mg的产率得到5-O-(4-azido-4,6-dideoxy-β-D-glucopyranosyl)-6-O-allyl-3',4'-di-O-benzyl-1-N-[(S)-2-benzyloxy-4-(benzyloxycarbonylamino)butanoyl]-3,2',6'-triazidoneamine
  参考文献：
  名称：

  Synthesis and antibacterial activity of pyranmycin derivatives with N-1 and O-6 modifications

  摘要：

  Continuing from our ongoing effort in modifying aminoglycoside antibiotics with the goal of counteracting drug resistant bacteria, we have further derivatized pyranmycin, a neomycin class aminoglycoside antibiotic, with modifications at O-6 and N-1 positions. The revealed SAR results demonstrated that the antibacterial activity of pyranmycin can be modulated by different acylic substituents at O-6. Among these results, the 6-O-aminoethyl derivative, JT050, showed effective activity against resistant strain Escherichia coli (pTZ19U-3) and E. coli (pSF815), which provides insight into further structural modi. cations. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.08.059