(1R)-(1,4:3,6-dianhydro-D-mannitol-2-yl)-1,4:3,6-dianhydro-D-fructose | 905988-41-2

• 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: (1R)-(1,4:3,6-dianhydro-D-mannitol-2-yl)-1,4:3,6-dianhydro-D-fructose
• 英文别名: (3R,3aR,5R,6aS)-5-[(3R,3aR,6R,6aS)-3,6-dihydroxy-3,3a,5,6a-tetrahydro-2H-furo[3,2-b]furan-6-yl]-3-hydroxy-2,3,3a,6a-tetrahydrofuro[3,2-b]furan-6-one
• CAS: 905988-41-2
• 化学式: C₁₂H₁₆O₈
• 分子量: 288.254
• InChiKey: RPNPZBYNCFGRDS-NZDDNSCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1R)-(1,4:3,6-dianhydro-D-mannitol-2-yl)-1,4:3,6-dianhydro-D-fructose 在 硫酸 、 硝酸 作用下， 以 二氯甲烷 为溶剂， 以92.6%的产率得到(1R)-(1,4:3,6-dianhydro-D-mannitol-2-yl)-1,4:3,6-dianhydro-D-fructose 5,5'-dinitrate
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.carres.2009.09.028
• 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 6.0h， 以80%的产率得到(1R)-(1,4:3,6-dianhydro-D-mannitol-2-yl)-1,4:3,6-dianhydro-D-fructose
  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

• Non-enzymatic kinetic resolution of β-amino alcohols using C-12 higher carbon sugar as a chiral auxiliary
  作者：Jing-Yu Zhang、Hong-Min Liu、Hai-Wei Xu、Li-Hong Shan

  DOI：10.1016/j.tetasy.2008.01.039

  日期：2008.3

  An efficient non-enzymatic kinetic resolution strategy capable of accessing optically active P-adrenergic antagonists intermediates is reported. The C-12 higher carbon sugar derived from naturally occurring sucrose was employed to probe the kinetic resolution. Excellent enantiomeric excesses (ee >99%) and high yields were obtained under very mild conditions. The chiral auxiliary could be recovered in a high reclaimed ratio (>95%) and reusable form without any decrease of the resolving ability. (C) 2008 Published by Elsevier Ltd.
• 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.
• 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.