methyl 4-O-(2-azidobenzyl)-6-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-α-D-mannopyranoside | 1380778-41-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: methyl 4-O-(2-azidobenzyl)-6-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-α-D-mannopyranoside
• 英文别名: [(3aS,4S,6R,7R,7aS)-7-[(2-azidophenyl)methoxy]-4-methoxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]methoxy-tert-butyl-dimethylsilane
• CAS: 1380778-41-5
• 化学式: C₂₃H₃₇N₃O₆Si
• 分子量: 479.649
• InChiKey: BHJJSVVMBTUPOH-MJCUULBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.43
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 4-O-(2-azidobenzyl)-6-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-α-D-mannopyranoside 在 四丁基氟化铵 、 potassium carbonate 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 methyl 4-O-(2-azidobenzyl)-5-ethynyl-2,3-O-isopropylidene-α-D-mannopyranoside
  参考文献：
  名称：

  Design and Synthesis of 1,2,3-Triazole-Fused Chiral Medium-Ring Benzo-Heterocycles, Scaffolds Mimicking Benzolactams

  摘要：

  Based on "amide-triazole bioequivalence" principle, 1,2,3-triazole-fused chiral medium ring benzo-heterocycles capable of mimicking benzolactams were designed. Their syntheses were accomplished by cycloaddition of different sugar-derived azidoalkynes. While triazole-fused eight-membered benzo-heterocycles were formed by exclusive intramolecuclar [3 + 2] cycloaddition, attempted preparation of seven-membered analogues led to some intermolecular cycloaddition resulting in a dimeric macrocyclic product, in addition to intramolecular cycloaddition furnishing the expected heterocycle.

  DOI：

  10.1021/jo3004327
• 作为产物：
  描述：

  1-叠氮基-2-(溴甲基)苯 、 甲基4-[(二乙氧基磷酰)(二氟)甲基]-N-{[(2-甲基-2-丙基)氧基]羰基}-L-苯丙氨酸酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 6.25h， 以79%的产率得到methyl 4-O-(2-azidobenzyl)-6-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-α-D-mannopyranoside
  参考文献：
  名称：

  Design and Synthesis of 1,2,3-Triazole-Fused Chiral Medium-Ring Benzo-Heterocycles, Scaffolds Mimicking Benzolactams

  摘要：

  Based on "amide-triazole bioequivalence" principle, 1,2,3-triazole-fused chiral medium ring benzo-heterocycles capable of mimicking benzolactams were designed. Their syntheses were accomplished by cycloaddition of different sugar-derived azidoalkynes. While triazole-fused eight-membered benzo-heterocycles were formed by exclusive intramolecuclar [3 + 2] cycloaddition, attempted preparation of seven-membered analogues led to some intermolecular cycloaddition resulting in a dimeric macrocyclic product, in addition to intramolecular cycloaddition furnishing the expected heterocycle.

  DOI：

  10.1021/jo3004327