(5S,6R,7R)-6,7-dihydro-5-(hydroxymethyl)-5H-pyrrolo<1,2-c>imidazole-6,7-diol | 136768-14-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (5S,6R,7R)-6,7-dihydro-5-(hydroxymethyl)-5H-pyrrolo<1,2-c>imidazole-6,7-diol
• 英文别名: (5S,6R,7R)-6,7-dihydro-5-hydroxymethyl-5H-pyrrolo<1,2-c>-imidazole-6,7-diol；(5S,6R,7R)-6,7-dihydro-5-(hydroxymethyl)-5H-pyrrolo[1,2-c]imidazole-6,7-diol；(5S,6R,7R)-5-(hydroxymethyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazole-6,7-diol
• CAS: 136768-14-4
• 化学式: C₇H₁₀N₂O₃
• 分子量: 170.168
• InChiKey: PLCUSYNYULFULB-RRKCRQDMSA-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：

  3,4,6-tri-O-benzyl-D-glucopyranose 在 palladium dihydroxide 吡啶 、 三氟甲磺酸酐 、 氨 、 氢气 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， -20.0~90.0 ℃ 、4.56 MPa 条件下， 反应 126.75h， 生成 (5S,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-#

文献信息

• Imidazole-Analogues of 6-Epicastanospermine and of 3,7a-Diepialexine
  作者：Andrzej Frankowski、Czeslawa Seliga、Daniel Bur、Jacques Streith

  DOI：10.1002/hlca.19910740503

  日期：1991.8.7

  were obtained from D-glucose derivative 9 by a sequence of selective protection/deprotection and intramolecular SN2 reactions. Triols 7 and 8 are analogues of 6-epica-stanospermine (4) and of 3,7a-diepialexine (6), respectively, and are potential glycosidase inhibitors. However, their anti-HIV activity proved to be only marginal.

  手性二环咪唑衍生物7和8是从d-葡萄糖衍生物得到9通过选择性保护/去保护序列和分子内小号Ñ 2反应。三元醇7和8分别是6-表皮-甜精胺（4）和3,7a-二哌阿西辛（6）的类似物，并且是潜在的糖苷酶抑制剂。但是，他们的抗艾滋病毒活性被证明只是微不足道的。
• 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).