1-N-(acetyl)-[N-(3,5-dinitro)-benzoyl]-2-deoxy-2-azido-4,6-O-benzylidene-α-D-glucopyranosyl amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 1-N-(acetyl)-[N-(3,5-dinitro)-benzoyl]-2-deoxy-2-azido-4,6-O-benzylidene-α-D-glucopyranosyl amine
• 英文别名: N-[(2R,4aR,6S,7R,8R,8aS)-7-azido-8-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]-N-acetyl-3,5-dinitrobenzamide
• 化学式: C₂₂H₂₀N₆O₁₀
• 分子量: 528.435
• InChiKey: AJAAAUHJSBSEHW-UFLNNZOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  38
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  191
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  3,5-二硝基苯甲酸 、 乙腈 、 pent-4-enyl 2-azido-2-deoxy-4,6-O-benzylidene-β-D-glucopyranoside 在 N-溴代丁二酰亚胺(NBS) 作用下， 反应 1.0h， 以99%的产率得到1-N-(acetyl)-[N-(3,5-dinitro)-benzoyl]-2-deoxy-2-azido-4,6-O-benzylidene-α-D-glucopyranosyl amine
  参考文献：
  名称：

  A Versatile, Three-Component-Reaction Route to N-Glycosylamines^,1

  摘要：

  [GRAPHICS]Under the agency of N-bromosuccinimide, n-pentenyl glycosides, acetonitrile, and carboxylic acids participate in th ree-component-reactions that afford N-acylated glycosylamines. The procedure tolerates diverse donors, and C2-tetrachlorophthalimido and CP-azido groups effectively control anomeric stereoselectivity, Success of the procedure does not appear to depend on the acid's strength, but for an aromatic acid, substitution pattern affects the rate, while the presence of a lone pair on the para substituent inhibits the process.

  DOI：

  10.1021/ol000265i

文献信息

• A Versatile, Three-Component-Reaction Route to <i>N</i>-Glycosylamines^,¹
  作者：Latha G. Nair、Bert Fraser-Reid、Anna Katrin Szardenings

  DOI：10.1021/ol000265i

  日期：2001.2.1

  [GRAPHICS]Under the agency of N-bromosuccinimide, n-pentenyl glycosides, acetonitrile, and carboxylic acids participate in th ree-component-reactions that afford N-acylated glycosylamines. The procedure tolerates diverse donors, and C2-tetrachlorophthalimido and CP-azido groups effectively control anomeric stereoselectivity, Success of the procedure does not appear to depend on the acid's strength, but for an aromatic acid, substitution pattern affects the rate, while the presence of a lone pair on the para substituent inhibits the process.