phenyl 6-deoxy-6-acetylamino-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 6-deoxy-6-acetylamino-β-D-glucopyranoside
• 英文别名: phenyl-(6-acetylamino-6-deoxy-β-D-glucopyranoside)；Phenyl-(6-acetylamino-6-desoxy-β-D-glucopyranosid)；N-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-phenoxy-tetrahydropyran-2-yl]methyl]acetamide；N-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-phenoxyoxan-2-yl]methyl]acetamide
• 化学式: C₁₄H₁₉NO₆
• 分子量: 297.308
• InChiKey: CANLSXYVMPZTCH-RKQHYHRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯基-BETA-葡萄糖吡喃糖苷 在 吡啶 、 sodium azide 、 三苯基膦 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 80.5h， 生成 phenyl 6-deoxy-6-acetylamino-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of novel HIV-1 protease inhibitors based on carbohydrate scaffolds

  摘要：

  The synthesis of peptidomimetic inhibitors of HIV-1 protease based on 6-deoxy-6-aniino-beta-D-glucopyranoside and 6-deoxy-6-amino- beta-D-mannopyranoside scaffolds has been achieved. The inhibitors had IC50 values in the micromolar range. The results provide a platform for the development of more potent carbohydrate based inhibitors of HIV-1 and other aspartic proteases. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00208-4

文献信息

• Helferich et al., Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1934, vol. 226, p. 258,261
  作者：Helferich et al.

  DOI：——

  日期：——
• Synthesis of novel HIV-1 protease inhibitors based on carbohydrate scaffolds
  作者：Paul V Murphy、Julie L O'Brien、Lorraine J Gorey-Feret、Amos B Smith

  DOI：10.1016/s0040-4020(03)00208-4

  日期：2003.3

  The synthesis of peptidomimetic inhibitors of HIV-1 protease based on 6-deoxy-6-aniino-beta-D-glucopyranoside and 6-deoxy-6-amino- beta-D-mannopyranoside scaffolds has been achieved. The inhibitors had IC50 values in the micromolar range. The results provide a platform for the development of more potent carbohydrate based inhibitors of HIV-1 and other aspartic proteases. (C) 2003 Elsevier Science Ltd. All rights reserved.