N-benzyl-2,6-di-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-2,6-di-O-pivaloyl-1,5-dideoxy-1,5-imino-D-mannitol
• 英文别名: [(2R,3R,4S,5R)-1-benzyl-5-(2,2-dimethylpropanoyloxy)-3,4-dihydroxypiperidin-2-yl]methyl 2,2-dimethylpropanoate
• 化学式: C₂₃H₃₅NO₆
• 分子量: 421.534
• InChiKey: KLSGPBLLGKIEBN-NCXUSEDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  96.3
• 氢给体数：
  2
• 氢受体数：
  7

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-2,6-di-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 an iminosugar based peptidomimetic analogue
  作者：Florence Chery、Paul V. Murphy

  DOI：10.1016/j.tetlet.2004.01.064

  日期：2004.3

  The synthesis of 1-deoxymannojirimycin based analogue of a known HIV-protease inhibitor is described. The strategies employed for introduction of the pharmocophore groups onto the azasugar scafford were based on regioselective reactions of the hydroxly groups of the natural product and of D-fructopyranoside derivatives. (C) 2004 Elsevier Ltd. All rights reserved.