2,6-di-O-pivaloyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-mannitol | 679404-78-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,6-di-O-pivaloyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-mannitol
• 英文别名: benzyl (2R,3R,4S,5R)-5-(2,2-dimethylpropanoyloxy)-2-(2,2-dimethylpropanoyloxymethyl)-3,4-dihydroxypiperidine-1-carboxylate
• CAS: 679404-78-5
• 化学式: C₂₄H₃₅NO₈
• 分子量: 465.544
• InChiKey: ZVXZCCGLMLEKSI-NCXUSEDFSA-N

物化性质

• 沸点：
  547.7±50.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,6-di-O-pivaloyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-mannitol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以61%的产率得到2,6-di-O-pivaloyl-1,5-dideoxy-1,5-imino-D-mannitol
  参考文献：
  名称：

  Synthesis of an iminosugar based peptidomimetic analogue

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2004.01.064
• 作为产物：
  描述：

  1-脱氧甘露伊霉素 在 吡啶 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 22.0h， 生成 2,6-di-O-pivaloyl-N-benzyloxycarbonyl-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.
• 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.