5-azido-5-deoxy-1,2-O-(1-methylethylidene)-3-O-trimethylsilyl-α-D-xylofuranose | 242148-37-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-azido-5-deoxy-1,2-O-(1-methylethylidene)-3-O-trimethylsilyl-α-D-xylofuranose
• CAS: 242148-37-4
• 化学式: C₁₁H₂₁N₃O₄Si
• 分子量: 287.391
• InChiKey: HDJJLIMVVJNGGD-UTINFBMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  85.68
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-azido-5-deoxy-1,2-O-(1-methylethylidene)-3-O-trimethylsilyl-α-D-xylofuranose 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以0.158 g的产率得到5-azido-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose
  参考文献：
  名称：

  Preparation of Primary and Secondary Azidosugars from Diols using the Dioxaphosphorane Methodology

  摘要：

  Treatment of methyl 2,3-di-O-benzyl-alpha-D-glucopyranoside (1), methyl 2,3-di-O-acetyl-alpha-D-glucopyranoside (4), 3-O-benzyl-1,2-O-(1-methylethylidene)-alpha-D-glucofuranose (6), 3-O-acetyl-1,2-O-(1-methylethylidene)-alpha-D-glucofuranose (9), 1,2-O-(1-methylethylidene)-alpha-D-xylofuranose (11) and methyl 2,3-di-O-acetyl-alpha-D-galactopyranoside (15) with diisopropylazodicarboxylate-triphenylphosphine in tetrahydrofuran led to the corresponding dioxaphosphoranes, which were opened by trimethylsilyl azide affording the silylated primary azidodeoxysugars. When the same reaction was performed on methyl 2,3-di-O-benzyl-alpha-D-galactopyranoside (20), an inversion of the regioselectivity of the dioxaphosphorane opening was observed, leading mainly to the 4-azido-4-deoxy-alpha-D-glucopyranoside derivative 27.

  DOI：

  10.1080/07328309908544029
• 作为产物：
  描述：

  叠氮基三甲基硅烷 、 1,2-O-异亚丙基-alpha-D-呋喃木糖 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 5-azido-5-deoxy-1,2-O-(1-methylethylidene)-3-O-trimethylsilyl-α-D-xylofuranose 、 1,2-O-(1-methylethylidene)-3,5-di-O-trimethylsilyl-α-D-xylofuranose
  参考文献：
  名称：

  Preparation of Primary and Secondary Azidosugars from Diols using the Dioxaphosphorane Methodology

  摘要：

  Treatment of methyl 2,3-di-O-benzyl-alpha-D-glucopyranoside (1), methyl 2,3-di-O-acetyl-alpha-D-glucopyranoside (4), 3-O-benzyl-1,2-O-(1-methylethylidene)-alpha-D-glucofuranose (6), 3-O-acetyl-1,2-O-(1-methylethylidene)-alpha-D-glucofuranose (9), 1,2-O-(1-methylethylidene)-alpha-D-xylofuranose (11) and methyl 2,3-di-O-acetyl-alpha-D-galactopyranoside (15) with diisopropylazodicarboxylate-triphenylphosphine in tetrahydrofuran led to the corresponding dioxaphosphoranes, which were opened by trimethylsilyl azide affording the silylated primary azidodeoxysugars. When the same reaction was performed on methyl 2,3-di-O-benzyl-alpha-D-galactopyranoside (20), an inversion of the regioselectivity of the dioxaphosphorane opening was observed, leading mainly to the 4-azido-4-deoxy-alpha-D-glucopyranoside derivative 27.

  DOI：

  10.1080/07328309908544029