4-[(1S,2R)-1,2,3-trihydroxypropyl]imidazole | 171895-34-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[(1S,2R)-1,2,3-trihydroxypropyl]imidazole
• 英文别名: (1S,2R)-1-(1(3)H-imidazol-4-yl)-propane-1,2,3-triol；(1S,2R)-1-(1(3)H-Imidazol-4-yl)-propan-1,2,3-triol；(1S,2R)-1-(1H-imidazol-5-yl)propane-1,2,3-triol
• CAS: 171895-34-4
• 化学式: C₆H₁₀N₂O₃
• 分子量: 158.157
• InChiKey: ABDKJICLXDSVKH-RITPCOANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  89.4
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[(1S,2R)-1,2,3-trihydroxypropyl]imidazole 在 吡啶 、 溶剂黄146 、 三乙胺 、 APTS 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 [(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-(1H-imidazol-5-yl)methyl] acetate
  参考文献：
  名称：

  New C2 symmetrical and semisymmetrical substituted imidazolium ribonucleoside. Imidazolic nucleosides analogues

  摘要：

  New C-2 symmetrical imidazolium ribonucleosides have been synthesized. The silyl Hilbert Johnson-Vorbrugen method was used. Subsequent coupling of trimethylsilylimidazole with the peracylated D-ribofuranose 1, followed by removal of the protecting groups, afforded 1,3-bis(beta-D-ribofuranosyl)imidazolium 7 and 1-(beta-D-ribofuranosyl)imidazole 8. In a similar synthetic sequence, 4(5)-substituted bis-ribofuranosylimidazolium 14 was also prepared, For the selective preparation of the monoglycosylated imidazole 15, the classical method starting from 2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide in acetonitrile and using Hg(CN)2 was employed. These new base modified nucleosides were devoid of activity against HIV and cytotoxicity. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(96)00453-3
• 作为产物：
  描述：

  (3-benzyl-3H-imidazol-4-yl)-acetic acid 在 palladium on activated charcoal 咪唑 、 盐酸 、 正丁基锂 、 MoO5*pyridine*HMPA 、 氢气 、 sodium hexamethyldisilazane 、 sodium hydride 、 二异丁基氢化铝 、 溶剂黄146 、 三乙胺 、 苄硫醇 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， -78.0 ℃ 、303.98 kPa 条件下， 反应 2.25h， 生成 4-[(1S,2R)-1,2,3-trihydroxypropyl]imidazole
  参考文献：
  名称：

  A versatile, enantioselective, stereocontrolled synthesis of (1S,2R)-imidazoleglycerol

  摘要：

  An efficient (21% overall yield), enantio- and diastereoselective, 11-step synthesis of (1S,2R)-imidazoleglycerol has been developed. The key steps are the stereoselective hydroxylation of an acyloxazolidinone enolate, the alkylation of a thioester with (MOMOCH(2))(2)CuLi and the stereodivergent reduction of the resulting ketone. The scope of the reaction of the enolate derived from 10 with heteroatom electrophiles has been studied. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02138-7

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。
• 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。
• Some New Naturally Occurring Imidazoles Related to the Biosynthesis of Histidine¹
  作者：Bruce N. Ames、Herschel K. Mitchell、Mary B. Mitchell

  DOI：10.1021/ja01101a001

  日期：1953.3
• Ames, Journal of Biological Chemistry, 1957, vol. 228, p. 131,135
  作者：Ames

  DOI：——

  日期：——
• New C2 symmetrical and semisymmetrical substituted imidazolium ribonucleoside. Imidazolic nucleosides analogues
  作者：A. Al Mourabit、M. Beckmann、C. Poupat、A. Ahond、P. Potier

  DOI：10.1016/s0957-4166(96)00453-3

  日期：1996.12

  New C-2 symmetrical imidazolium ribonucleosides have been synthesized. The silyl Hilbert Johnson-Vorbrugen method was used. Subsequent coupling of trimethylsilylimidazole with the peracylated D-ribofuranose 1, followed by removal of the protecting groups, afforded 1,3-bis(beta-D-ribofuranosyl)imidazolium 7 and 1-(beta-D-ribofuranosyl)imidazole 8. In a similar synthetic sequence, 4(5)-substituted bis-ribofuranosylimidazolium 14 was also prepared, For the selective preparation of the monoglycosylated imidazole 15, the classical method starting from 2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide in acetonitrile and using Hg(CN)2 was employed. These new base modified nucleosides were devoid of activity against HIV and cytotoxicity. Copyright (C) 1996 Elsevier Science Ltd.