(5R,6S,7R)-5-Hydroxymethyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole-6,7-diol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (5R,6S,7R)-5-Hydroxymethyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole-6,7-diol
• 英文别名: (5R,6S,7R)-5-(hydroxymethyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole-6,7-diol
• 化学式: C₇H₁₀N₂O₃
• 分子量: 170.168
• InChiKey: DGGMEKMJNMCZQN-SRQIZXRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  78.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2S,3S,4R)-3,4-Bis-benzyloxy-4-(1H-imidazol-2-yl)-butane-1,2-diol 在 palladium on activated charcoal 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 三氟甲磺酸酐 、 四丁基氟化铵 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、3.0 MPa 条件下， 反应 182.0h， 生成 (5R,6S,7R)-5-Hydroxymethyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole-6,7-diol
  参考文献：
  名称：

  Carbohydrate transition state mimics: synthesis of imidazolo-Pyrrolidinoses as potential nectrisine surrogates

  摘要：

  The syntheses of four glyco-imidazoles, which are pentose-derivatives belonging to the D-series, as well as the syntheses of their (L)-enantiomers, are reported. Starting from the known linear xylo, lyxo, arabino, and ribo imidazolo-pentoses in both the Land the D-series, intramolecular Walden inversion led to the corresponding arabino, ribo, xylo, and lyxo pyrrolidinopentoses in the (D)- and the (L)-series, respectively, protection and deprotection steps being unavoidable prerequisites. The structures and configurations of all eight pyrrolidinopentoses were determined unambiguously, by a combination of H-1/C-13 NMR spectroscopy, circular dichroism and [alpha](D) values, in conjunction with single-crystal X-ray diffraction analysis of the (L)-xylo stereoisomer. Examination of the inhibitory properties of these imidazolo-pyrrolidinoses against six commonly encountered glycosidases led to the conclusion that by and large the (L)-stereoisomers are inactive, whereas three out the four (D)-stereoisomers proved to be poor to moderate inhibitors. It appears therefore that the most basic N(1) atom is not located in an optimal topology to be protonated easily inside the enzyme's active site. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00402-4

文献信息

• Carbohydrate transition state mimics: synthesis of imidazolo-Pyrrolidinoses as potential nectrisine surrogates
  作者：Théophile Tschamber、François Gessier、Estelle Dubost、Jeffery Newsome、Céline Tarnus、Josiane Kohler、Markus Neuburger、Jacques Streith

  DOI：10.1016/s0968-0896(03)00402-4

  日期：2003.8

  The syntheses of four glyco-imidazoles, which are pentose-derivatives belonging to the D-series, as well as the syntheses of their (L)-enantiomers, are reported. Starting from the known linear xylo, lyxo, arabino, and ribo imidazolo-pentoses in both the Land the D-series, intramolecular Walden inversion led to the corresponding arabino, ribo, xylo, and lyxo pyrrolidinopentoses in the (D)- and the (L)-series, respectively, protection and deprotection steps being unavoidable prerequisites. The structures and configurations of all eight pyrrolidinopentoses were determined unambiguously, by a combination of H-1/C-13 NMR spectroscopy, circular dichroism and [alpha](D) values, in conjunction with single-crystal X-ray diffraction analysis of the (L)-xylo stereoisomer. Examination of the inhibitory properties of these imidazolo-pyrrolidinoses against six commonly encountered glycosidases led to the conclusion that by and large the (L)-stereoisomers are inactive, whereas three out the four (D)-stereoisomers proved to be poor to moderate inhibitors. It appears therefore that the most basic N(1) atom is not located in an optimal topology to be protonated easily inside the enzyme's active site. (C) 2003 Elsevier Ltd. All rights reserved.