4-(α-D-erythrofuranosyl)-1-(methyl 2-deoxy-α-D-glucopyranosid-2-yl)-4-imidazoline-2-thione | 250265-42-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(α-D-erythrofuranosyl)-1-(methyl 2-deoxy-α-D-glucopyranosid-2-yl)-4-imidazoline-2-thione
• 英文别名: Zevvrqaibczvdn-nflypbgesa-；3-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]-5-[(2R,3R,4R)-3,4-dihydroxyoxolan-2-yl]-1H-imidazole-2-thione
• CAS: 250265-42-0
• 化学式: C₁₄H₂₂N₂O₈S
• 分子量: 378.403
• InChiKey: ZEVVRQAIBCZVDN-NFLYPBGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  176
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 4-(α-D-erythrofuranosyl)-1-(methyl 2-deoxy-α-D-glucopyranosid-2-yl)-4-imidazoline-2-thione 在 吡啶 作用下， 反应 12.0h， 以81%的产率得到4-(2,3-di-O-acetyl-α-D-erythrofuranosyl)-1-(methyl-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosid-2-yl)-4-imidazoline-2-thione
  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
• 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 69.67h， 生成 4-(α-D-erythrofuranosyl)-1-(methyl 2-deoxy-α-D-glucopyranosid-2-yl)-4-imidazoline-2-thione
  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

文献信息

• Stereoselective synthesis of imidazolidine, imidazoline and imidazole C- and N-pseudonucleosides
  作者：José G Fernández-Bolaños、Encarnación Zafra、Oscar López、Inmaculada Robina、José Fuentes

  DOI：10.1016/s0957-4166(99)00314-6

  日期：1999.7

  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.