4-(β-D-erythrofuranosyl)-1-(methyl 2-deoxy-α-D-glucopyranosid-2-yl)-4-methylthio-1H-imidazole

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(β-D-erythrofuranosyl)-1-(methyl 2-deoxy-α-D-glucopyranosid-2-yl)-4-methylthio-1H-imidazole
• 英文别名: (2R,3S,4R,5R,6S)-5-[4-[(2S,3R,4R)-3,4-dihydroxyoxolan-2-yl]-2-methylsulfanylimidazol-1-yl]-2-(hydroxymethyl)-6-methoxyoxane-3,4-diol
• 化学式: C₁₅H₂₄N₂O₈S
• 分子量: 392.43
• InChiKey: BGRMYRJWGRUDGR-NCKBLKPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  172
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  Methyl 2-benzamido-2-deoxy-α-D-glucopyranoside 在 sodium hydroxide 、 溶剂黄146 、 三氟乙酸 作用下， 反应 203.67h， 生成 4-(β-D-erythrofuranosyl)-1-(methyl 2-deoxy-α-D-glucopyranosid-2-yl)-4-methylthio-1H-imidazole
  参考文献：
  名称：

  Stereoselective synthesis of imidazolidine, imidazoline and imidazole C- and N-pseudonucleosides

  摘要：

  Methyl 2-deoxy-2-isothiocyanato-alpha-D-glucopyranoside 2, which exists in equilibrium with the corresponding 2,3-cyclic carbamate 1, reacts with D-glucosamine producing the pseudo-C and N-nucleoside of chiral imidazolidine-2-thione 3, in good yield and high stereoselectivity. Starting from 3, different pseudo-C- and N-nucleosides of imidazoline-2-thione 6-11, and of imidazole 12 and 13 are obtained. Conformational aspects of some of the prepared compounds are discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00314-6