4(5)-(L-xylotetritol-1-yl)imidazole | 172016-35-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4(5)-(L-xylotetritol-1-yl)imidazole
• 英文别名: 4-[(1R,2S,3S)-1,2,3,4-tetrahydroxybutyl]imidazole；4-(L-xylo-Tetrahydroxybutyl)-imidazol；1-(1(3)H-imidazol-4-yl)-butane-1,2,3,4-tetraol；(1R,2S,3S)-1-(1H-imidazol-5-yl)butane-1,2,3,4-tetrol
• CAS: 172016-35-2
• 化学式: C₇H₁₂N₂O₄
• 分子量: 188.183
• InChiKey: NFARKZJOWDCJHH-RRKCRQDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4(5)-(L-xylotetritol-1-yl)imidazole 在 palladium dihydroxide 吡啶 、 4-二甲氨基吡啶 、 三氟甲磺酸酐 、 氢气 、 四丁基碘化铵 、 sodium hydride 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， -55.0~75.0 ℃ 、101.33 kPa 条件下， 反应 54.0h， 生成 (5R,6R,7R)-6,7-dihydro-5-hydroxymethyl-5H-pyrrolo<1,2-c>-imidazole-6,7-diol
  参考文献：
  名称：

  The Synthesis of Imidazol Sugars Which Mimic Cyclic Carboxonium Ions Formed During the Glycosidase‐Catalysed Hydrolysis of Oligo and Polysaccharides

  摘要：

  Some naturally occurring carbohydrates, of which several hydroxy groups had been selectively protected, were condensed with formamidine to give the expected imidazole derivatives in the D-arabino (9), D-lyxo (12), L-xylo (17), D-threo (21), and in the L- and D-erythro (24) series. Introduction of a strong leaving group at the remaining free alcohol function of these products led at once to intramolecular S(N)2 cyclisation to the corresponding bicyclic aza sugar derivatives. This was followed by total deprotection to give the target aza sugars in the L-xylo (7), L-ribo (14), D-arabino (19), as well as in the D-threo (22) and the L- and D-erythro (26) series. Inhibitory assays with four glycosidases showed that the D-arabino aza sugar 19 is the only potent inhibitor (for an alpha-mannosidase of jack bean).

  DOI：

  10.1002/(sici)1099-0690(199904)1999:4<893::aid-ejoc893>3.0.co;2-#
• 作为产物：
  描述：

  L-sorbopyranose 、 醋酸甲脒 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 4(5)-(L-xylotetritol-1-yl)imidazole
  参考文献：
  名称：

  天然单糖合成手性离子液体

  摘要：

  含有咪唑鎓、吡唑鎓和双苯并咪唑鎓的离子液体由容易获得的、未受保护的碳水化合物如d-核糖、d-木糖、d-葡萄糖、d-半乳糖、d-果糖和l-山梨糖合成。

  DOI：

  10.1002/ejoc.202200100

文献信息

• On the Way to Glycoprocessing Inhibitors: A General One-Pot Synthesis of Imidazolosugars
  作者：Jacques Streith、Arnaud Boiron、Andrzej Frankowski、Didier Le Nouen、Hélène Rudyk、Théophile Tschamber

  DOI：10.1055/s-1995-4040

  日期：1995.8

  Reaction of several monosaccharides with formamidine acetate afforded the corresponding imidazolosugars 5-11 in 30-50% yield.

  几种单糖与甲酰胺乙酸反应，在30-50%的产率下得到了相应的咪唑糖5-11。
• The Synthesis of Imidazol Sugars Which Mimic Cyclic Carboxonium Ions Formed During the Glycosidase‐Catalysed Hydrolysis of Oligo and Polysaccharides
  作者：Jacques Streith、Hélène Rudyk、Théophile Tschamber、Céline Tarnus、Christiane Strehler、Dariusz Deredas、Andrzej Frankowski

  DOI：10.1002/(sici)1099-0690(199904)1999:4<893::aid-ejoc893>3.0.co;2-#

  日期：1999.4

  Some naturally occurring carbohydrates, of which several hydroxy groups had been selectively protected, were condensed with formamidine to give the expected imidazole derivatives in the D-arabino (9), D-lyxo (12), L-xylo (17), D-threo (21), and in the L- and D-erythro (24) series. Introduction of a strong leaving group at the remaining free alcohol function of these products led at once to intramolecular S(N)2 cyclisation to the corresponding bicyclic aza sugar derivatives. This was followed by total deprotection to give the target aza sugars in the L-xylo (7), L-ribo (14), D-arabino (19), as well as in the D-threo (22) and the L- and D-erythro (26) series. Inhibitory assays with four glycosidases showed that the D-arabino aza sugar 19 is the only potent inhibitor (for an alpha-mannosidase of jack bean).
• Synthesis of Chiral Ionic Liquids from Natural Monosaccharides
  作者：Mattia Ghirardello、Maira Costantini、Alessandra Vecchi、Salvatore Pacifico、Daniele Pazzi、Franca Castiglione、Andrea Mele、Alberto Marra

  DOI：10.1002/ejoc.202200100

  日期：2022.6.7

  Imidazolium-, pyrazolium-, and bis-benzimidazolium-containing ionic liquids were synthesized from easily available, unprotected carbohydrates such as d-ribose, d-xylose, d-glucose, d-galactose, d-fructose and l-sorbose.

  含有咪唑鎓、吡唑鎓和双苯并咪唑鎓的离子液体由容易获得的、未受保护的碳水化合物如d-核糖、d-木糖、d-葡萄糖、d-半乳糖、d-果糖和l-山梨糖合成。