(1R,2S,3R)-1-(4'-imidazolyl)-1,2,4-tri-O-benzylbutane-1,2,3,4-tetrol | 223410-17-1

• 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: (1R,2S,3R)-1-(4'-imidazolyl)-1,2,4-tri-O-benzylbutane-1,2,3,4-tetrol
• 英文别名: (2R,3S,4R)-4-(1H-imidazol-5-yl)-1,3,4-tris(phenylmethoxy)butan-2-ol
• CAS: 223410-17-1
• 化学式: C₂₈H₃₀N₂O₄
• 分子量: 458.557
• InChiKey: AYSWLCUOBDPAFA-FCEKVYKBSA-N

物化性质

• 沸点：
  678.796±55.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.218±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  76.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2S,3R)-1-(4'-imidazolyl)-1,2,4-tri-O-benzylbutane-1,2,3,4-tetrol 在 吡啶 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 (5S,6S,7R)-6,7-Bis-benzyloxy-5-benzyloxymethyl-6,7-dihydro-5H-pyrrolo[1,2-c]imidazole
  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-#
• 作为产物：
  描述：

  3,4,5-tri-O-benzyl-D-galactopyranose 、 醋酸甲脒 在 氨 作用下， 90.0 ℃ 、4.56 MPa 条件下， 反应 30.0h， 以30%的产率得到(1R,2S,3R)-1-(4'-imidazolyl)-1,2,4-tri-O-benzylbutane-1,2,3,4-tetrol
  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

• 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).