1-azido-1-deoxy-L-ribitol | 178900-06-6

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 1-azido-1-deoxy-L-ribitol
• 英文别名: (2S,3R,4R)-5-azidopentane-1,2,3,4-tetrol
• CAS: 178900-06-6
• 化学式: C₅H₁₁N₃O₄
• 分子量: 177.16
• InChiKey: ZYIOBOVNJFAAOK-MROZADKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  95.3
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-azido-1-deoxy-L-ribitol 在 palladium on activated charcoal ammonium formate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以98%的产率得到1-amino-1-deoxy-L-ribitol
  参考文献：
  名称：

  Efficient syntheses of 1-bromodeoxy-, 1-azidodeoxy- and 1-aminodeoxypentitols from unprotected d-pentono-1,4-lactones

  摘要：

  The reduction of unprotected 5-bromo-5-deoxy-D-ribono, D-arabinono and D-xylono-1,4-lactones was achieved with NaBH4 in water-EtOH. The corresponding 1-bromo-1-deoxypentitols were isolated after acetylation in good overall yields (60-90%). 1-Azido-1-deoxypentitols were obtained quantitatively either by nucleophilic substitution by azide ion and deacetylation of the corresponding monobromopentitols or by reduction of the corresponding 5-azido-5-deoxy-D-pentono-1,4-lactones. The reduction of the monoazidopentitols by catalytic hydrogen transfer gave the monoaminopentitol analogues in quantitative yield.

  DOI：

  10.1016/s0008-6215(99)00261-x
• 作为产物：
  描述：

  5-bromo-5-deoxy-D-ribono-1,4-lactone 在 sodium tetrahydroborate 、 叠氮化锂 、 Amberlite IR-120H⁺ 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 1-azido-1-deoxy-L-ribitol
  参考文献：
  名称：

  Efficient syntheses of 1-bromodeoxy-, 1-azidodeoxy- and 1-aminodeoxypentitols from unprotected d-pentono-1,4-lactones

  摘要：

  The reduction of unprotected 5-bromo-5-deoxy-D-ribono, D-arabinono and D-xylono-1,4-lactones was achieved with NaBH4 in water-EtOH. The corresponding 1-bromo-1-deoxypentitols were isolated after acetylation in good overall yields (60-90%). 1-Azido-1-deoxypentitols were obtained quantitatively either by nucleophilic substitution by azide ion and deacetylation of the corresponding monobromopentitols or by reduction of the corresponding 5-azido-5-deoxy-D-pentono-1,4-lactones. The reduction of the monoazidopentitols by catalytic hydrogen transfer gave the monoaminopentitol analogues in quantitative yield.

  DOI：

  10.1016/s0008-6215(99)00261-x

文献信息

• A new efficient way to α,ω-diaminoitols by direct azidation of unprotected itols
  作者：V. Glaçon、A. El Meslouti、R. Uzan、G. Demailly、D. Beaupère

  DOI：10.1016/0040-4039(96)00618-1

  日期：1996.5

  Unprotected pentitols and erythritol are transformed into α,ω-diazido derivatives by successive treatment with thionyl chloride and sodium azide. Reduction by catalytic hydrogen transfer gives the α,ω-diaminoitols.

  通过用亚硫酰氯和叠氮化钠相继处理，将未保护的戊糖醇和赤藓糖醇转化为α，ω-二叠氮基衍生物。通过催化氢转移还原得到α，ω-二氨基醇。
• Efficient syntheses of 1-bromodeoxy-, 1-azidodeoxy- and 1-aminodeoxypentitols from unprotected d-pentono-1,4-lactones
  作者：Véronique Bouchez、Imane Stasik、Daniel Beaupère

  DOI：10.1016/s0008-6215(99)00261-x

  日期：1999.1

  The reduction of unprotected 5-bromo-5-deoxy-D-ribono, D-arabinono and D-xylono-1,4-lactones was achieved with NaBH4 in water-EtOH. The corresponding 1-bromo-1-deoxypentitols were isolated after acetylation in good overall yields (60-90%). 1-Azido-1-deoxypentitols were obtained quantitatively either by nucleophilic substitution by azide ion and deacetylation of the corresponding monobromopentitols or by reduction of the corresponding 5-azido-5-deoxy-D-pentono-1,4-lactones. The reduction of the monoazidopentitols by catalytic hydrogen transfer gave the monoaminopentitol analogues in quantitative yield.