3,5-di-O-levulinoyl-4-O-pivaloyl-1,2-O-isopropylidene-β-D-fructopyranose | 679404-84-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,5-di-O-levulinoyl-4-O-pivaloyl-1,2-O-isopropylidene-β-D-fructopyranose
• 英文别名: [(5S,6S,7R,8R)-7-(2,2-dimethylpropanoyloxy)-2,2-dimethyl-6-(4-oxopentanoyloxy)-1,3,10-trioxaspiro[4.5]decan-8-yl] 4-oxopentanoate
• CAS: 679404-84-3
• 化学式: C₂₄H₃₆O₁₁
• 分子量: 500.543
• InChiKey: VOLUHKQRMIXLBF-QJHDXQOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3,5-di-O-levulinoyl-4-O-pivaloyl-1,2-O-isopropylidene-β-D-fructopyranose 在 palladium on activated charcoal 吡啶 、 sodium azide 、 氢气 、 一水合肼 、 溶剂黄146 、 三氟乙酸 、 二溴三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 68.0h， 生成 [(2R,3R,4R,5R)-4-(2,2-dimethylpropanoyloxy)-3,5-dihydroxypiperidin-2-yl]methyl 2,2-dimethylpropanoate
  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：

  3-O-levulinoyl-1,2-O-isopropylidene-β-D-fructopyranose 在 吡啶 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 3,5-di-O-levulinoyl-4-O-pivaloyl-1,2-O-isopropylidene-β-D-fructopyranose
  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.