methyl 3-azido-2,3-dideoxy-β-D-erythro-pentofuranoside | 114071-67-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: methyl 3-azido-2,3-dideoxy-β-D-erythro-pentofuranoside
• 英文别名: methyl 3-azido-2,3-dideoxy-β-D-erythro-pentafuranoside；[(2S,3S,5R)-3-azido-5-methoxyoxolan-2-yl]methanol
• CAS: 114071-67-9
• 化学式: C₆H₁₁N₃O₃
• 分子量: 173.172
• InChiKey: HBHRHEDVWOWVDS-KVQBGUIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  53
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-azido-2,3-dideoxy-β-D-erythro-pentofuranoside 在 吡啶 、 三正丁基氢锡 、 sodium iodide 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 12.25h， 生成 methyl 3-acetamido-2,3,5-trideoxy-5-C-(ethoxyisopropylphosphinyl)-β-D-erythro-pentofuranoside
  参考文献：
  名称：

  Synthesis and structural analyses of 3-acetamido-1,4-di-O-acetyl-2,3,5-trideoxy-5-C-(isopropylphosphinyl)-d-erythro-pentopyranoses

  摘要：

  H-1 NMR spectroscopy of phosphorus containing hetero sugars (phospha sugars), revealed the alpha and beta configurations and chair conformations for 3-acetamido-1,4-di-O-acetyl-2,3,5-trideoxy-5-C-(isopropylphosphinyl)-alpha- and beta-D-erythro-pentopyranoses. The conformation of the title compounds was determined by H-1 NMR as C-1(4) in CDCl3 and the conformation was in accord with that in solid state determined by X-ray crystallographic analysis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00397-x
• 作为产物：
  描述：

  Methanesulfonic acid (2R,3S,4R,5R)-5-methoxy-4-methylsulfanylthiocarboxyoxy-2-trityloxymethyl-tetrahydro-furan-3-yl ester 在 盐酸 、 sodium azide 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 5.0h， 生成 methyl 3-azido-2,3-dideoxy-β-D-erythro-pentofuranoside
  参考文献：
  名称：

  Synthesis and structural analyses of 3-acetamido-1,4-di-O-acetyl-2,3,5-trideoxy-5-C-(isopropylphosphinyl)-d-erythro-pentopyranoses

  摘要：

  H-1 NMR spectroscopy of phosphorus containing hetero sugars (phospha sugars), revealed the alpha and beta configurations and chair conformations for 3-acetamido-1,4-di-O-acetyl-2,3,5-trideoxy-5-C-(isopropylphosphinyl)-alpha- and beta-D-erythro-pentopyranoses. The conformation of the title compounds was determined by H-1 NMR as C-1(4) in CDCl3 and the conformation was in accord with that in solid state determined by X-ray crystallographic analysis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00397-x