4(5)-(D-arabinotetritol-1-yl)-imidazole | 340699-23-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4(5)-(D-arabinotetritol-1-yl)-imidazole
• 英文别名: 4(5)-(D-lyxotetritol-1-yl)imidazole；4-[(1R,2R,3R)-1,2,3,4-tetrahydroxybutyl]imidazole；(1R)-1-(1(3)H-imidazol-4-yl)-D-threitol；(1R)-1-(1(3)H-Imidazol-4-yl)-D-threit；(1R,2R,3R)-1-(1H-imidazol-5-yl)butane-1,2,3,4-tetrol
• CAS: 340699-23-2
• 化学式: C₇H₁₂N₂O₄
• 分子量: 188.183
• InChiKey: NFARKZJOWDCJHH-QYNIQEEDSA-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)-(D-arabinotetritol-1-yl)-imidazole 在 sodium periodate 作用下， 以 水 为溶剂， 生成 4-咪唑甲醛
  参考文献：
  名称：

  Mass spectrometry of imidazole-4(5)-carboxaldehyde and some 1-methyl and nitro derivatives

  摘要：

  AbstractThe mass spectra of imidazole‐4(5)‐carboxaldehyde, its two 1‐methyl derivatives, 4(5)‐nitroimidazole, 5(4)‐nitroimidazole‐4(5)‐carboxaldehyde and 1‐methyl‐5‐nitroimidazole‐4‐carboxaldehyde are presented and discussed in comparison with those of other imidazole‐carboxaldehydes and nitroimidazoles earlier reported. The imidazole‐carboxaldehydes and their 1‐methyl derivatives exhibit the characteristic fragmentation of aromatic aldehydes, and differences between the isomers can be observed. The nitroimidazoles show the fragmentation typical of aromatic nitrocompounds. In the o‐nitroimidazole‐carboxaldehydes, the typical losses of aldehydes do not occur, but primary ortho effects between the formyl and nitro groups give rise to important fragmentation routes. In their 1‐methyl derivatives, the presence of the methyl group adjacent to the nitro group originates additional double and secondary ortho effects. For some of these transformations, fragmentation mechanisms are proposed.

  DOI：

  10.1002/oms.1210210810
• 作为产物：
  描述：

  口服葡萄糖 在 ammonium hydroxide 、 copper(II) oxide 作用下， 生成 4(5)-(D-arabinotetritol-1-yl)-imidazole 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Parrod, Bulletin de la Societe Chimique de France, 1932, vol. <4> 51, p. 1424,1426

  摘要：

  DOI：

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。
• Stereoisomeric Imidazolo-Pentoses − Synthesis, Chiroptical Properties, and Evaluation as Glycosidase Inhibitors
  作者：Théophile Tschamber、Hervé Siendt、Arnaud Boiron、François Gessier、Dariusz Deredas、Andrzej Frankowski、Sylviane Picasso、Heinz Steiner、Anne-Marie Aubertin、Jacques Streith

  DOI：10.1002/1099-0690(200104)2001:7<1335::aid-ejoc1335>3.0.co;2-z

  日期：2001.4

  The syntheses of all four imidazolo-piperidino-pentoses in the L-series ent-2 to ent-5, and of three out of the four possible stereomers in the D-series 3, 4, and 5, are reported. The linear imidazolo sugar precursors were prepared, either by double condensation of formamidine with protected aldohexoses, or by nucleophilic addition of a lithiated imidazole derivative to protected aldotetroses. Cyclisation

  报告了 L 系列 ent-2 至 ent-5 中所有四种咪唑并哌啶基戊糖的合成，以及 D 系列 3、4 和 5 中四种可能立体异构体中三种的合成。线性咪唑并糖前体通过甲脒与受保护的己醛糖的双重缩合或通过锂化咪唑衍生物与受保护的醛四糖的亲核加成来制备。这些线性咪唑并碳水化合物的环化是通过分子内 SN2 反应进行的。然后对目标分子进行脱保护。四对相反的对映体在其 CD 光谱中显示出明显的镜像型棉花效应。D 系列的所有立体异构体都显示负旋光度 ([α]D)，而 L 系列的立体异构体显示正旋光度。八种咪唑并糖均不抑制 HIV-1 的复制。根据 Michaelis-Menten 动力学确定，其中一些被证明是相当有选择性的，但只是中等有效的 α-糖苷酶抑制剂。
• 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。