(2S,3S,4S,5R,6R)-3,4-Diazido-5-benzyloxy-2-benzyloxymethyl-6-[(1S,2S,3R,4S,6R)-4,6-diazido-3-((2R,3R,5S,6R)-3-azido-6-azidomethyl-5-benzyloxy-tetrahydro-pyran-2-yloxy)-2-benzyloxy-cyclohexyloxy]-tetrahydro-pyran | 738602-06-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S,4S,5R,6R)-3,4-Diazido-5-benzyloxy-2-benzyloxymethyl-6-[(1S,2S,3R,4S,6R)-4,6-diazido-3-((2R,3R,5S,6R)-3-azido-6-azidomethyl-5-benzyloxy-tetrahydro-pyran-2-yloxy)-2-benzyloxy-cyclohexyloxy]-tetrahydro-pyran
• CAS: 738602-06-7
• 化学式: C₄₆H₅₀N₁₈O₈
• 分子量: 983.019
• InChiKey: BYNNTKQTDOFDQB-RTKPLLSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.68
• 重原子数：
  72.0
• 可旋转键数：
  24.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  366.4
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6R)-3,4-Diazido-5-benzyloxy-2-benzyloxymethyl-6-[(1S,2S,3R,4S,6R)-4,6-diazido-3-((2R,3R,5S,6R)-3-azido-6-azidomethyl-5-benzyloxy-tetrahydro-pyran-2-yloxy)-2-benzyloxy-cyclohexyloxy]-tetrahydro-pyran 在 水 、 三甲基膦 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Glyco-optimization of aminoglycosides: new aminoglycosides as novel anti-infective agents

  摘要：

  Glyco-optimization (OPopS(TM)) of aminoglycosides has been performed by replacing the existing sugar moiety with a variety of sugar derivatives. Glycosylation of the 6-position of nebramine provided a library of novel 4,6-linked aminoglycosides (AMGs). Among them, compounds 8b,g,i,l, and 8u with 2"-amino, 2",3"-diamino, 2",4"-diamino, 3,4"-diamino, 3"-amino groups, respectively, showed significant antimicrobial activity against Gram-(+) and -(-) bacteria. Several were particularly potent against Pseudomonus aeruginosa with MICs in the 1-2 mug/mL range. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.004
• 作为产物：
  描述：

  penta-azidotobramycin 在 N-碘代丁二酰亚胺 、 硫酸 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.33h， 生成 (2S,3S,4S,5R,6R)-3,4-Diazido-5-benzyloxy-2-benzyloxymethyl-6-[(1S,2S,3R,4S,6R)-4,6-diazido-3-((2R,3R,5S,6R)-3-azido-6-azidomethyl-5-benzyloxy-tetrahydro-pyran-2-yloxy)-2-benzyloxy-cyclohexyloxy]-tetrahydro-pyran
  参考文献：
  名称：

  Glyco-optimization of aminoglycosides: new aminoglycosides as novel anti-infective agents

  摘要：

  Glyco-optimization (OPopS(TM)) of aminoglycosides has been performed by replacing the existing sugar moiety with a variety of sugar derivatives. Glycosylation of the 6-position of nebramine provided a library of novel 4,6-linked aminoglycosides (AMGs). Among them, compounds 8b,g,i,l, and 8u with 2"-amino, 2",3"-diamino, 2",4"-diamino, 3,4"-diamino, 3"-amino groups, respectively, showed significant antimicrobial activity against Gram-(+) and -(-) bacteria. Several were particularly potent against Pseudomonus aeruginosa with MICs in the 1-2 mug/mL range. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.004