1,3,2',6'-tetraazido-5-O-methoxymethyl-6,3',4'-tri-O-acetylneamine | 937021-96-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,2',6'-tetraazido-5-O-methoxymethyl-6,3',4'-tri-O-acetylneamine
• 英文别名: [(1S,2S,3R,4S,6R)-4,6-diazido-3-[(2R,3R,4R,5R,6R)-4,5-diacetyloxy-3-azido-6-(azidomethyl)oxan-2-yl]oxy-2-(methoxymethoxy)cyclohexyl] acetate
• CAS: 937021-96-0
• 化学式: C₂₀H₂₈N₁₂O₁₀
• 分子量: 596.517
• InChiKey: NRXGBYUBWZAXPL-QTZWXDKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  42
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  173
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  1,3,2',6'-tetraazido-5-O-methoxymethyl-6,3',4'-tri-O-acetylneamine 在 sodium periodate 、 potassium tert-butylate 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 [(1S,2S,3R,4S,6R)-4,6-diazido-3-[(1S,2R)-2-azido-1-[(2R)-1-azido-3-oxopropan-2-yl]oxy-3-oxopropoxy]-2-(methoxymethoxy)cyclohexyl] acetate
  参考文献：
  名称：

  A Short and Scalable Route to Orthogonally O-Protected 2-Deoxystreptamine

  摘要：

  A seven-step synthesis of orthogonally O-protected 2-deoxy-streptamine has been developed from readily available neomycin, with an overall yield of 28%. Key chemical transformations include a chemoselective glycosidic bond hydrolysis and two regioselective protective group manipulations involving acetylation and deacetylation. The synthetic route is amenable to scale-up for the production of multigram quantities of enantiopure and orthogonally O-protected 2-deoxystreptamine, a versatile scaffold for the generation of libraries of RNA-targeting ligands.

  DOI：

  10.1021/jo062369y
• 作为产物：
  描述：

  1,3,2′,6′-tetraazidoneamine 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 1,3,2',6'-tetraazido-5-O-methoxymethyl-6,3',4'-tri-O-acetylneamine
  参考文献：
  名称：

  A Short and Scalable Route to Orthogonally O-Protected 2-Deoxystreptamine

  摘要：

  A seven-step synthesis of orthogonally O-protected 2-deoxy-streptamine has been developed from readily available neomycin, with an overall yield of 28%. Key chemical transformations include a chemoselective glycosidic bond hydrolysis and two regioselective protective group manipulations involving acetylation and deacetylation. The synthetic route is amenable to scale-up for the production of multigram quantities of enantiopure and orthogonally O-protected 2-deoxystreptamine, a versatile scaffold for the generation of libraries of RNA-targeting ligands.

  DOI：

  10.1021/jo062369y