5-azido-5-deoxy-D-arabinono-1,4-lactone | 182575-41-3

• 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-D-arabinono-1,4-lactone
• 英文别名: (3S,4S,5R)-5-(azidomethyl)-3,4-dihydroxyoxolan-2-one
• CAS: 182575-41-3
• 化学式: C₅H₇N₃O₄
• 分子量: 173.128
• InChiKey: TVYMNCLFKDIJNE-JJYYJPOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  81.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-azido-5-deoxy-D-arabinono-1,4-lactone 在 palladium on activated charcoal sodium tetrahydroborate 、 Amberlite IR-120H⁺ 、 ammonium formate 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 1-amino-1-deoxy-D-lyxitol
  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：

  1,2-O-isopropylidene-5-O-toluene-p-sulphonyl-β-D-arabinofuranose 在 sodium azide 、 Dowex 50 W (H⁺) 、 溴 、 尿素 、 barium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.75h， 生成 5-azido-5-deoxy-D-arabinono-1,4-lactone
  参考文献：
  名称：

  Synthesis of 5-Amino-5-deoxypentonolactams

  摘要：

  从D-木糖和D-阿拉伯糖开始制备5-Azido-5-deoxy-1,2-O-异丙基亚-α-D-木糖呋喃糖（4）和5-azido-5-deoxy-1,2-O-异丙基亚-β-D-阿拉伯呋喃糖（10）。使用氧化还原法进行C-3异构化，从4和10分别得到5-azido-5-deoxy-1,2-O-异丙基亚-α-D-核糖呋喃糖（15）和5-azido-5-deoxy-1,2-O-异丙基亚-β-D-莱克索呋喃糖（17）。通过酸水解、溴氧化和催化氢化，分别得到相应的5-azido-5-deoxy-D-戊糖呋喃糖6、11、18、19，5-azido-5-deoxy-D-戊内酯7、12、20、21和5-氨基-5-deoxy-D-戊内酰胺8、13、22、23。

  DOI：

  10.1135/cccc19961027

文献信息

• A concise synthesis of 5-amino-5-deoxyaldonic acids as monomers for the preparation of nylon 5
  作者：Céline Falentin、Daniel Beaupère、Gilles Demailly、Imane Stasik

  DOI：10.1016/j.carres.2007.09.008

  日期：2007.12

  Saponification of 5-azido-5-deoxy-D-pentonolactones (ribo-, arabino-, xylo-) with NaOH gave the corresponding 5-azido-5-deoxyaldonic acids sodium salts which, after regeneration of the acid form followed by catalytic reduction, led to the target compounds in 98% overall yields.

  将5-叠氮基5-脱氧-D-戊内酯（核糖，阿拉伯糖，木糖基）用NaOH皂化，得到相应的5-叠氮基5-脱氧醛糖醛酸钠盐，其在酸形式再生后催化还原，以98％的总收率得到目标化合物。
• An efficient and facile three-step synthesis of 5-amino-5-deoxy-D-pentonolactams from unprotected D-pentono-1,4-lactones.
  作者：Véronique Bouchez、Imane Stasik、Daniel Beaupère、Raoul Uzan

  DOI：10.1016/s0040-4039(97)10065-x

  日期：1997.11

  Regioselective bromination of D-pentono-1,4-lactones with SOBr2 in DMF led to 5-bromo-5-deoxy derivatives. These intermediates were treated with LiN3 and hydrogenated to give 5-amino-5-deoxy-D-pentonolactams in 60-83% overall yield. (C) 1997 Elsevier Science Ltd.