methyl (3R,4R)-5-azido-2,5-dideoxy-α,β-pentofuranoside | 955999-12-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (3R,4R)-5-azido-2,5-dideoxy-α,β-pentofuranoside
• 英文别名: methyl 5-azido-2,5-dideoxy-D-xylofuranoside；(2R,3R)-2-(azidomethyl)-5-methoxyoxolan-3-ol
• CAS: 955999-12-9
• 化学式: C₆H₁₁N₃O₃
• 分子量: 173.172
• InChiKey: NLMMFSMYHJUSMB-QYRBDRAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 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 (3R,4R)-5-azido-2,5-dideoxy-α,β-pentofuranoside 在 吡啶 、 叠氮化锂 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 methyl (3S,4R)-3,5-diazido-2,3,5-trideoxy-α,β-pentofuranoside
  参考文献：
  名称：

  Synthesis of Different 3,5‐Diazidofuranoses: A New and General Synthesis Pathway

  摘要：

  Diamino- and diazidofuranoses represent useful precursors, for example, for the synthesis of substituted nucleosides and metal complexes, respectively. Known procedures for their synthesis lack the availability of cheap starting materials, adequate yields, and the access to all possible diastereomeres. Therefore, 3,5-diazido-3,5-dideoxy- and - 2,3,5- trideoxyfuranoses both with ribo- and xylo- configuration were prepared using different approaches.

  DOI：

  10.1080/07328300701540175
• 作为产物：
  描述：

  2-deoxy-D-ribose 在 15-冠醚-5 吡啶 、 叠氮化锂 、 硫酸 、 水 、 sodium nitrite 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 methyl (3R,4R)-5-azido-2,5-dideoxy-α,β-pentofuranoside
  参考文献：
  名称：

  Synthesis of Different 3,5‐Diazidofuranoses: A New and General Synthesis Pathway

  摘要：

  Diamino- and diazidofuranoses represent useful precursors, for example, for the synthesis of substituted nucleosides and metal complexes, respectively. Known procedures for their synthesis lack the availability of cheap starting materials, adequate yields, and the access to all possible diastereomeres. Therefore, 3,5-diazido-3,5-dideoxy- and - 2,3,5- trideoxyfuranoses both with ribo- and xylo- configuration were prepared using different approaches.

  DOI：

  10.1080/07328300701540175

文献信息

• Graef, Silke; Braun, Manfred, Liebigs Annalen der Chemie, 1993, # 10, p. 1091 - 1098
  作者：Graef, Silke、Braun, Manfred

  DOI：——

  日期：——
• Synthesis of Different 3,5‐Diazidofuranoses: A New and General Synthesis Pathway
  作者：Daniel Koth、Andrea Fiedler、Sandy Scholz、Michael Gottschaldt

  DOI：10.1080/07328300701540175

  日期：2007.9

  Diamino- and diazidofuranoses represent useful precursors, for example, for the synthesis of substituted nucleosides and metal complexes, respectively. Known procedures for their synthesis lack the availability of cheap starting materials, adequate yields, and the access to all possible diastereomeres. Therefore, 3,5-diazido-3,5-dideoxy- and - 2,3,5- trideoxyfuranoses both with ribo- and xylo- configuration were prepared using different approaches.