N-benzyl-6-O-pivaloyl-1,5-dideoxy-1,5-imino-D-mannitol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-benzyl-6-O-pivaloyl-1,5-dideoxy-1,5-imino-D-mannitol
• 英文别名: [(2R,3R,4R,5R)-1-benzyl-3,4,5-trihydroxypiperidin-2-yl]methyl 2,2-dimethylpropanoate
• 化学式: C₁₈H₂₇NO₅
• 分子量: 337.416
• InChiKey: QVCLVOXXTFPGOD-KLHDSHLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  90.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-脱氧甘露伊霉素 在 palladium on activated charcoal 吡啶 、 氢气 、 碳酸氢钠 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 N-benzyl-6-O-pivaloyl-1,5-dideoxy-1,5-imino-D-mannitol
  参考文献：
  名称：

  Synthesis of peptidomimetics based on iminosugar and β-d-glucopyranoside scaffolds and inhibiton of HIV-protease

  摘要：

  Synthetic routes to peptidomimetic compounds derived from saccharide scaffolds are described. The regioselective introduction of pivaloyl groups was achieved from N-benzyloxycarbonyl protected 1-deoxymannojirimycin or via D-fructopyranosides. The results from biological evaluation of the saccharide derivatives as HIV-protease inhibitors are included. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.080

文献信息

• Synthesis of peptidomimetics based on iminosugar and β-d-glucopyranoside scaffolds and inhibiton of HIV-protease
  作者：Florence Chery、Linda Cronin、Julie L O'Brien、Paul V Murphy

  DOI：10.1016/j.tet.2004.05.080

  日期：2004.7

  Synthetic routes to peptidomimetic compounds derived from saccharide scaffolds are described. The regioselective introduction of pivaloyl groups was achieved from N-benzyloxycarbonyl protected 1-deoxymannojirimycin or via D-fructopyranosides. The results from biological evaluation of the saccharide derivatives as HIV-protease inhibitors are included. (C) 2004 Elsevier Ltd. All rights reserved.