1,4-anhydro-D-fructose

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 1,4-anhydro-D-fructose
• 英文别名: (4S,5R)-5-[(1R)-1,2-dihydroxyethyl]-4-hydroxyoxolan-3-one
• 化学式: C₆H₁₀O₅
• 分子量: 162.142
• InChiKey: QMKUJGYJIQIANY-UYFOZJQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,2-O-异亚丙基-D-呋喃葡萄糖 在 palladium dihydroxide sodium tetrahydroborate 、 氢气 、 sodium hydride 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 79.0h， 生成 1,4-anhydro-D-fructose
  参考文献：
  名称：

  Synthesis of 1,4-anhydro-d-fructose and 1,4-anhydro-d-tagatose

  摘要：

  1,4-Anhydro-D-fructose and 1,4-anhydro-D-tagatose were prepared from 1,2-O-isopropylidene-D-glucofuranose via the common intermediate 3,5,6-tri-O-benzyl-D-glucitol. The title compounds may be interesting anti-oxidants and feature activities akin to their natural pyranoid counterpart, 1,5-anhydro-D-fructose. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.001

文献信息

• [EN] 1,5 AND 1,4-ANHYDROKETOSES, METHODS FOR THE PREPARATION OF 1,5-AND 1,4-ANHYDROKETOSES, INTERMEDIATES, AND USES OF 1,5-AND 1,4-ANHYDROKETOSES<br/>[FR] 1,5- ET 1,4-ANHYDROCETOSES, PROCEDES DE PREPARATION DE 1,5- ET 1,4-ANHYDROCETOSES, INTERMEDIAIRES, ET UTILISATIONS DE 1,5- ET 1,4-ANHYDROCETOSES
  申请人：GLYCOM APS

  公开号：WO2005121114A2

  公开（公告）日：2005-12-22

  The present invention relates to 1,4- and 1,5-anhydro-D-ketoses (monosaccharides, oligosaccharides and various glycoconjugates), e.g. 1,5-anhydro-D-fructose. Moreover, the invention provides synthetic methods and novel intermediates and precursors suitable for their preparation. The methods include catalytic- and/or pyrolitic sulfenic acid elimination of corresponding ß-hydroxy sulfoxides, N-deprotection of N-substituted-aminoglycals, O-deprotection of carbohydrate enolethers and/or O-acyl-substituted carbohydrate enols, and regio- and stereoselective modification and subsequent chemical transformation of bicyclic and/or tricyclic 1,4- and 1,5-anhydro-glycoderivatives. Furthermore, the present invention provides novel applications of 1,4- and 1,5-anhydroketoses within pharmaceutical, food and cosmetic industries.
• Synthesis of 1,4-anhydro-d-fructose and 1,4-anhydro-d-tagatose
  作者：Gyula Dekany、Inge Lundt、Andreas J. Steiner、Arnold E. Stütz

  DOI：10.1016/j.carres.2006.03.001

  日期：2006.7

  1,4-Anhydro-D-fructose and 1,4-anhydro-D-tagatose were prepared from 1,2-O-isopropylidene-D-glucofuranose via the common intermediate 3,5,6-tri-O-benzyl-D-glucitol. The title compounds may be interesting anti-oxidants and feature activities akin to their natural pyranoid counterpart, 1,5-anhydro-D-fructose. (c) 2006 Elsevier Ltd. All rights reserved.