3-azido-6-azidomethyl-4,5-bis-benzyloxy-2-(4-benzyloxy-2-benzyloxymethyl-5-methoxy-tetrahydro-furan-3-yloxy)-tetrahydro-pyran | 474266-86-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-azido-6-azidomethyl-4,5-bis-benzyloxy-2-(4-benzyloxy-2-benzyloxymethyl-5-methoxy-tetrahydro-furan-3-yloxy)-tetrahydro-pyran
• 英文别名: (2S,3R,4R,5R,6R)-5-azido-2-(azidomethyl)-6-[(2R,3R,4R,5R)-5-methoxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxolan-3-yl]oxy-3,4-bis(phenylmethoxy)oxane
• CAS: 474266-86-9
• 化学式: C₄₀H₄₄N₆O₈
• 分子量: 736.825
• InChiKey: JSUZNJQBOVWMON-KMCCIDMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  54
• 可旋转键数：
  19
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3-azido-6-azidomethyl-4,5-bis-benzyloxy-2-(4-benzyloxy-2-benzyloxymethyl-5-methoxy-tetrahydro-furan-3-yloxy)-tetrahydro-pyran 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 4.25h， 生成 3-azido-6-azidomethyl-4,5-bis-benzyloxy-2-p-tolylsulfanyl-tetrahydro-pyran
  参考文献：
  名称：

  Reexamination of Neomycin B Degradation:  Efficient Preparation of Its CD and D Rings as Protected Glycosyl Donors

  摘要：

  [GRAPHICS]The degradation of neomycin B was reexamined, and a novel protocol was established to prepare the properly masked neomycin CD ring as a glycol donor in excellent yield. Glycosylation of the CD ring with glycol acceptors provided a facile access to versatile intermediates that could be utilized to synthesize a variety of novel neomycin B mimetics for RNA recognition.

  DOI：

  10.1021/ol026548n
• 作为产物：
  描述：

  甲醇 、 hexaazido-hepta-O-benzyl neomycin 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 14.0h， 以82%的产率得到1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine
  参考文献：
  名称：

  Reexamination of Neomycin B Degradation:  Efficient Preparation of Its CD and D Rings as Protected Glycosyl Donors

  摘要：

  [GRAPHICS]The degradation of neomycin B was reexamined, and a novel protocol was established to prepare the properly masked neomycin CD ring as a glycol donor in excellent yield. Glycosylation of the CD ring with glycol acceptors provided a facile access to versatile intermediates that could be utilized to synthesize a variety of novel neomycin B mimetics for RNA recognition.

  DOI：

  10.1021/ol026548n

文献信息

• Reexamination of Neomycin B Degradation:  Efficient Preparation of Its CD and D Rings as Protected Glycosyl Donors
  作者：Baogen Wu、Jun Yang、Yun He、Eric E. Swayze

  DOI：10.1021/ol026548n

  日期：2002.10.1

  [GRAPHICS]The degradation of neomycin B was reexamined, and a novel protocol was established to prepare the properly masked neomycin CD ring as a glycol donor in excellent yield. Glycosylation of the CD ring with glycol acceptors provided a facile access to versatile intermediates that could be utilized to synthesize a variety of novel neomycin B mimetics for RNA recognition.