6-azido-6-deoxy-D-mannitol | 906340-99-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-azido-6-deoxy-D-mannitol
• 英文别名: (2R,3R,4R,5R)-6-azidohexane-1,2,3,4,5-pentol
• CAS: 906340-99-6
• 化学式: C₆H₁₃N₃O₅
• 分子量: 207.186
• InChiKey: BPWHMSFNUDJDKX-KVTDHHQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  116
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-azido-6-deoxy-D-mannitol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以98%的产率得到1-氨基-1-脱氧-D-甘露糖醇
  参考文献：
  名称：

  The direct synthesis of 6-amino-6-deoxyaldonic acids as monomers for the preparation of polyhydroxylated nylon 6

  摘要：

  6-Azido-6-deoxy-D-galactitol and D-mannitol were obtained quantitatively via the reduction of the corresponding 6-azido-6deoxy-D-hexono-1,4-lactones, and 6-azido-6-deoxy-D-glucitol was obtained by the reduction of 6-azido-6-deoxyglucose in good yields. The reduction of monoazidodeoxyhexitols by catalytic hydrogenation gave the monoaminohexitol analogues in 95-98% yields. Oxidation of these afforded the corresponding 6-amino-6-deoxy-D-aldonic acids in moderate yields. Alternatively, saponification of 6-azido-6-deoxy-D-hexonolactones gave 6-azido-6-deoxyaldonic acid salts which, after reduction followed by neutralization, led to the expected compounds in 82-88% overall yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.04.018
• 作为产物：
  描述：

  D-甘露糖-1,4-内酯 在 sodium tetrahydroborate 、 叠氮化锂 、 四溴化碳 、 三苯基膦 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 6-azido-6-deoxy-D-mannitol
  参考文献：
  名称：

  The direct synthesis of 6-amino-6-deoxyaldonic acids as monomers for the preparation of polyhydroxylated nylon 6

  摘要：

  6-Azido-6-deoxy-D-galactitol and D-mannitol were obtained quantitatively via the reduction of the corresponding 6-azido-6deoxy-D-hexono-1,4-lactones, and 6-azido-6-deoxy-D-glucitol was obtained by the reduction of 6-azido-6-deoxyglucose in good yields. The reduction of monoazidodeoxyhexitols by catalytic hydrogenation gave the monoaminohexitol analogues in 95-98% yields. Oxidation of these afforded the corresponding 6-amino-6-deoxy-D-aldonic acids in moderate yields. Alternatively, saponification of 6-azido-6-deoxy-D-hexonolactones gave 6-azido-6-deoxyaldonic acid salts which, after reduction followed by neutralization, led to the expected compounds in 82-88% overall yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.04.018

文献信息

• Importance of topology for glycocluster binding to Pseudomonas aeruginosa and Burkholderia ambifaria bacterial lectins
  作者：Caroline Ligeour、Lucie Dupin、Anthony Angeli、Gérard Vergoten、Sébastien Vidal、Albert Meyer、Eliane Souteyrand、Jean-Jacques Vasseur、Yann Chevolot、François Morvan

  DOI：10.1039/c5ob01445j

  日期：——

  Pseudomonas aeruginosa and Burkholderia ambifaria are two opportunistic bacteria and major infectious agents involved in infection of cystic fibrosis patients.

  铜绿假单胞菌和安比法尔布氏杆菌是两种机会性细菌，是导致囊性纤维化患者感染的主要传染病原体。
• The direct synthesis of 6-amino-6-deoxyaldonic acids as monomers for the preparation of polyhydroxylated nylon 6
  作者：Ludovic Chaveriat、Imane Stasik、Gilles Demailly、Daniel Beaupère

  DOI：10.1016/j.tetasy.2006.04.018

  日期：2006.5

  6-Azido-6-deoxy-D-galactitol and D-mannitol were obtained quantitatively via the reduction of the corresponding 6-azido-6deoxy-D-hexono-1,4-lactones, and 6-azido-6-deoxy-D-glucitol was obtained by the reduction of 6-azido-6-deoxyglucose in good yields. The reduction of monoazidodeoxyhexitols by catalytic hydrogenation gave the monoaminohexitol analogues in 95-98% yields. Oxidation of these afforded the corresponding 6-amino-6-deoxy-D-aldonic acids in moderate yields. Alternatively, saponification of 6-azido-6-deoxy-D-hexonolactones gave 6-azido-6-deoxyaldonic acid salts which, after reduction followed by neutralization, led to the expected compounds in 82-88% overall yields. (c) 2006 Elsevier Ltd. All rights reserved.