2-C-aminomethyl-1,4:3,6-dianhydromannitol | 879288-27-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: 2-C-aminomethyl-1,4:3,6-dianhydromannitol
• 英文别名: 2-C-aminomethylisomannide；2-C-(Aminomethyl)-1,4:3,6-dianhydro-D-mannitol；(3R,3aR,6R,6aS)-6-(aminomethyl)-3,3a,5,6a-tetrahydro-2H-furo[3,2-b]furan-3,6-diol
• CAS: 879288-27-4
• 化学式: C₇H₁₃NO₄
• 分子量: 175.185
• InChiKey: QFJOBHNVFUZJJE-MVIOUDGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-C-aminomethyl-1,4:3,6-dianhydromannitol 、 (1R)-(1,4:3,6-dianhydro-D-mannitol-2-yl)-1,4:3,6-dianhydro-D-fructose 在 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以86%的产率得到(2R,3R,3aS,6R,6aR,3'R,3'aS,6'R,6'aR,5''R,6'''R,7'''R,8'''S)-dispiro[6,3',6'-trihydroxy-octahydro[2,3']bi[furo[3,2-b]furan]-3,2''-[1'',3''-oxazolidine]-5'',3'''-[6'''-hydroxy-tetrahydro-furo[3,2-b]furan]]
  参考文献：
  名称：

  A novel free C-12 higher carbon sugar: asymmetric synthesis and reactivity with nucleophiles

  摘要：

  A novel C-12 higher carbon sugar, (1R)-(1,4:3,6-dianhydro-D-mannitol-2-yl)- 1,4:3,6-dianhydro-D-fructose, was firstly synthesized via a convenient aldol reaction of 1,4:3,6-dianhydro-D-fructose without any protection and activation of functional groups. The reactivity of the novel higher sugar with nucleophiles was also studied, through which a series of oxazolidines and other derivatives of the higher sugar were available. The study showed that the higher sugar possesses a highly reactive carbonyl group and a good stereo controlling ability in the reaction. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.042
• 作为产物：
  描述：

  1,4:3,6-dianhydro-D-fructose 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 为溶剂， 20.0~50.0 ℃ 、344.74 kPa 条件下， 反应 10.0h， 生成 2-C-aminomethyl-1,4:3,6-dianhydromannitol
  参考文献：
  名称：

  新的氨基糖衍生物的高度立体选择性合成和结构表征。

  摘要：

  通过硝基烷基与1,4：3,6-双脱水果糖的亨利反应合成2-C-硝基烷基-1,4：3,6-双脱水甘露醇。然后催化氢化得到相应的邻位氨基醇。用羟胺氧化1，4：3，6-二脱水果糖，然后氢化，得到2-氨基-1，4：3，6-二脱水-2-脱氧甘露糖醇。通过HRMS，1H NMR，13C NMR和IR光谱阐明了所有化合物。通过单晶X射线分析或NOESY光谱研究证实了氨基糖衍生物的绝对构型。提出了硝基2-C-硝基烷基糖加氢的可能机理。提出了硝基和氨基糖衍生物的稠合呋喃环的构象。

  DOI：

  10.1016/j.carres.2005.11.019

文献信息

• A novel free C-12 higher carbon sugar: asymmetric synthesis and reactivity with nucleophiles
  作者：Hong-Min Liu、Feng-Wu Liu、Xiao-Ping Song、Jing-Yu Zhang、Lin Yan

  DOI：10.1016/j.tetasy.2006.11.042

  日期：2006.12

  A novel C-12 higher carbon sugar, (1R)-(1,4:3,6-dianhydro-D-mannitol-2-yl)- 1,4:3,6-dianhydro-D-fructose, was firstly synthesized via a convenient aldol reaction of 1,4:3,6-dianhydro-D-fructose without any protection and activation of functional groups. The reactivity of the novel higher sugar with nucleophiles was also studied, through which a series of oxazolidines and other derivatives of the higher sugar were available. The study showed that the higher sugar possesses a highly reactive carbonyl group and a good stereo controlling ability in the reaction. (c) 2006 Elsevier Ltd. All rights reserved.
• Highly stereoselective synthesis and structural characterization of new amino sugar derivatives
  作者：Feng-Wu Liu、Lin Yan、Jing-Yu Zhang、Hong-Min Liu

  DOI：10.1016/j.carres.2005.11.019

  日期：2006.2

  Catalytic hydrogenation then afforded the corresponding vicinal amino alcohols. Oximation of 1,4:3,6-dianhydrofructose with hydroxylamine, followed by hydrogenation, gave 2-amino-1,4:3,6-dianhydro-2-deoxymannitol. All compounds were elucidated by their HRMS, 1H NMR, 13C NMR, and IR spectra. The absolute configurations of the amino sugar derivatives were confirmed by single-crystal X-ray analysis or

  通过硝基烷基与1,4：3,6-双脱水果糖的亨利反应合成2-C-硝基烷基-1,4：3,6-双脱水甘露醇。然后催化氢化得到相应的邻位氨基醇。用羟胺氧化1，4：3，6-二脱水果糖，然后氢化，得到2-氨基-1，4：3，6-二脱水-2-脱氧甘露糖醇。通过HRMS，1H NMR，13C NMR和IR光谱阐明了所有化合物。通过单晶X射线分析或NOESY光谱研究证实了氨基糖衍生物的绝对构型。提出了硝基2-C-硝基烷基糖加氢的可能机理。提出了硝基和氨基糖衍生物的稠合呋喃环的构象。