O2-(3,4,6-tri-O-acetyl-β-D-N-acetylglucosaminyl)1-[N-(propargylaminocarbonylmethyl)-N-methylamino]diazen-1-ium-1,2-diolate | 1246199-58-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O2-(3,4,6-tri-O-acetyl-β-D-N-acetylglucosaminyl)1-[N-(propargylaminocarbonylmethyl)-N-methylamino]diazen-1-ium-1,2-diolate
• 英文别名: [OA-1-63]
• CAS: 1246199-58-5
• 化学式: C₂₀H₂₉N₅O₁₁
• 分子量: 515.477
• InChiKey: WFVZFMUNHHGNJB-RUGGUXRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.87
• 重原子数：
  36.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  197.23
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  5,5-di(azidomethyl)-2-phenyl-1,3-dioxane 、 O2-(3,4,6-tri-O-acetyl-β-D-N-acetylglucosaminyl)1-[N-(propargylaminocarbonylmethyl)-N-methylamino]diazen-1-ium-1,2-diolate 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 为溶剂， 以63%的产率得到[OA-1-154]
  参考文献：
  名称：

  “Click” Reaction in Conjunction with Diazeniumdiolate Chemistry: Developing High-Load Nitric Oxide Donors

  摘要：

  The use of Cu(I)-catalyzed "click" reactions of alkyne-substituted diazeniumdiolate prodrugs with bis- and tetrakis-azido compounds is described. The "click" reaction for the bis-azide using CuSO4/Na-ascorbate predominantly gave the expected bis-triazole. However, CuI/diisopropylethylamine predominantly gave uncommon triazolo-triazole products as a result of oxidative coupling. Neither set of "click" conditions showed evidence of compromising the integrity of the diazeniumdiolate groups. The chemistry developed has applications in the synthesis of polyvalent and dendritic nitric oxide donors.

  DOI：

  10.1021/ol101645k
• 作为产物：
  描述：

  O(2)-(3,4,6-tri-O-acetyl-N-acetyl-β-D-glucosaminyl) 1-[N-(2-carboxymethyl)-N-methylamino]diazen-1-ium-1,2-diolate 、 炔丙胺 在 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 3.17h， 以66%的产率得到O2-(3,4,6-tri-O-acetyl-β-D-N-acetylglucosaminyl)1-[N-(propargylaminocarbonylmethyl)-N-methylamino]diazen-1-ium-1,2-diolate
  参考文献：
  名称：

  “Click” Reaction in Conjunction with Diazeniumdiolate Chemistry: Developing High-Load Nitric Oxide Donors

  摘要：

  The use of Cu(I)-catalyzed "click" reactions of alkyne-substituted diazeniumdiolate prodrugs with bis- and tetrakis-azido compounds is described. The "click" reaction for the bis-azide using CuSO4/Na-ascorbate predominantly gave the expected bis-triazole. However, CuI/diisopropylethylamine predominantly gave uncommon triazolo-triazole products as a result of oxidative coupling. Neither set of "click" conditions showed evidence of compromising the integrity of the diazeniumdiolate groups. The chemistry developed has applications in the synthesis of polyvalent and dendritic nitric oxide donors.

  DOI：

  10.1021/ol101645k