((5R,6S,7S)-6,7-Bis-benzyloxy-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-5-yl)-methanol | 647017-26-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ((5R,6S,7S)-6,7-Bis-benzyloxy-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-5-yl)-methanol
• CAS: 647017-26-3
• 化学式: C₂₁H₂₂N₂O₃
• 分子量: 350.417
• InChiKey: JVSMDZBBKNTBLS-HSALFYBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  56.51
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ((5R,6S,7S)-6,7-Bis-benzyloxy-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-5-yl)-methanol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 水 为溶剂， 20.0 ℃ 、3.0 MPa 条件下， 反应 72.0h， 以80%的产率得到(5R,6S,7S)-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
• 作为产物：
  描述：

  (2S,3S,4S)-3,4-Bis-benzyloxy-4-(1H-imidazol-2-yl)-butane-1,2-diol 在 吡啶 、 4-二甲氨基吡啶 、 三氟甲磺酸酐 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 ((5R,6S,7S)-6,7-Bis-benzyloxy-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-5-yl)-methanol
  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