(1S)-(1,4:3,6-dianhydro-D-mannitol-2-yl)-2-nitromethyl-1,4:3,6-dianhydro-D-glucitol | 929548-42-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S)-(1,4:3,6-dianhydro-D-mannitol-2-yl)-2-nitromethyl-1,4:3,6-dianhydro-D-glucitol
• 英文别名: (2R,3R,3aS,6R,6aR,3'R,3'aS,6'R,6'aR)-3,6,3',6'-tetrahydroxy-3-nitromethyl-octahydro[2,3']bi[furo[3,2-b]furan]
• CAS: 929548-42-5
• 化学式: C₁₃H₁₉NO₁₀
• 分子量: 349.295
• InChiKey: YEXGHDZJPJDYJC-PEANUBHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.59
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  160.98
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (1S)-(1,4:3,6-dianhydro-D-mannitol-2-yl)-2-nitromethyl-1,4:3,6-dianhydro-D-glucitol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 50.0 ℃ 、344.74 kPa 条件下， 反应 8.0h， 以89%的产率得到(2R,3R,3aS,6R,6aR,3'R,3'aS,6'R,6'aR)-3-aminomethyl-3,6,3',6'-tetrahydroxy-octahydro[2,3']bi[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 三乙胺 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 (1S)-(1,4:3,6-dianhydro-D-mannitol-2-yl)-2-nitromethyl-1,4:3,6-dianhydro-D-glucitol
  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

文献信息

• The Henry reaction of (1R)-(1,4:3,6-dianhydro-d-mannitol-2-yl)-1,4:3,6-dianhydro-d-fructose 5,5′-dinitrate. Different reactive features of nitromethane to nitroethane
  作者：Feng-Wu Liu、Zhen-Ji Wang、Xiao-Ping Song、Sai-Yang Zhang、Hong-Min Liu

  DOI：10.1016/j.carres.2009.09.028

  日期：2009.12

  Henry reactions of a novel higher sugar derivative, (1R)-(1,4:3,6-dianhydro-D-mannitol-2-yl)-1,4:3,6-dianhydro-D-fructose 5,5'-dinitrate (Alternate nomenclature: (1R)-(isomannid-2-yl)-1,4:3,6-dianhydro-D-fructose 5,5'-dinitrate), with nitromethane and nitroethane were studied. The kinetic and thermodynamic reactions with nitromethane under different conditions were carried out to afford (2S)- and (2R)-beta-nitroalcohols, respectively. But when using nitroethane the reaction gave a (2S)-beta-nitroalcohol with an inverted configuration at vicinal carbon C-1. Two stereogenic centers were generated, and one was altered in the reaction. (C) 2009 Elsevier Ltd. All rights reserved.