phenyl 3-O-pivaloyl-4,6-O-benzylidene-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 3-O-pivaloyl-4,6-O-benzylidene-β-D-glucopyranoside
• 英文别名: [(4aR,6S,7R,8R,8aR)-7-hydroxy-6-phenoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 2,2-dimethylpropanoate
• 化学式: C₂₄H₂₈O₇
• 分子量: 428.482
• InChiKey: KVGYPGJRLMLAJR-RPVYJRQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  苯甲醛二甲缩醛 、 三甲基乙酰氯 、 苯基-BETA-葡萄糖吡喃糖苷 在 camphor-10-sulfonic acid 、 吡啶 作用下， 以 乙腈 为溶剂， 反应 16.0h， 生成 phenyl 3-O-pivaloyl-4,6-O-benzylidene-β-D-glucopyranoside 、 phenyl 3,6-di-O-pivaloyl-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

• 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.