1-azido-1-deoxy-L-xylitol | 178757-82-9

• 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-xylitol
• 英文别名: (2S,3S,4R)-5-azidopentane-1,2,3,4-tetrol
• CAS: 178757-82-9
• 化学式: C₅H₁₁N₃O₄
• 分子量: 177.16
• InChiKey: ZYIOBOVNJFAAOK-WISUUJSJSA-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-xylitol 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-xylitol
  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：

  Xylitol 在 咪唑 、 氯化亚砜 、 sodium azide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 1-azido-1-deoxy-L-xylitol
  参考文献：
  名称：

  Synthesis of α,ω‐Diazidoalditol Derivatives via Both bis‐ or tris‐Cyclic Sulfites and Peracetylated α,ω‐Dibromoalditols as Bielectrophilic Intermediates

  摘要：

  The alpha,omega-diazidoalditol derivatives with erythro, threo, xylo, ribo, D-arabino, D-manno, and D-gluco configuration were efficiently synthesized, respectively, from bis- or tris-cyclic sulfite or peracetylated alpha,omega-dibromoalditol intermediates. The cyclic sulfite intermediates has the advantage to lead directly to the free alpha,omega-diazido-alpha,omega-dideoxyalditols.

  DOI：

  10.1081/car-120030470

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。
• Synthesis of α,ω‐Diazidoalditol Derivatives via Both <i>bis</i>‐ or <i>tris</i>‐Cyclic Sulfites and Peracetylated α,ω‐Dibromoalditols as Bielectrophilic Intermediates
  作者：Virginie Glaçon、Mohammed Benazza、Aniss El Anzi、Daniel Beaupère、Gilles Demailly

  DOI：10.1081/car-120030470

  日期：2004.12.26

  The alpha,omega-diazidoalditol derivatives with erythro, threo, xylo, ribo, D-arabino, D-manno, and D-gluco configuration were efficiently synthesized, respectively, from bis- or tris-cyclic sulfite or peracetylated alpha,omega-dibromoalditol intermediates. The cyclic sulfite intermediates has the advantage to lead directly to the free alpha,omega-diazido-alpha,omega-dideoxyalditols.
• 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.