phenyl 6-azido-6-deoxy-3-O-benzyl-2-O-triisopropylsilyl-β-D-glucopyranoside | 760966-09-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 6-azido-6-deoxy-3-O-benzyl-2-O-triisopropylsilyl-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6S)-2-(azidomethyl)-6-phenoxy-4-phenylmethoxy-5-tri(propan-2-yl)silyloxyoxan-3-ol
• CAS: 760966-09-4
• 化学式: C₂₈H₄₁N₃O₅Si
• 分子量: 527.736
• InChiKey: JPGFUTOVCBUOTF-RKFAPSRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.61
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 6-azido-6-deoxy-3-O-benzyl-2-O-triisopropylsilyl-β-D-glucopyranoside 在 Lindlar's catalyst 氢气 、 sodium hydride 作用下， 以 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 5.5h， 生成
  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
• 作为产物：
  描述：

  phenyl 3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 在 吡啶 、 2,6-二甲基吡啶 、 sodium azide 、 Amberlite IR-120 (plus) 、 sodium 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.08h， 生成 phenyl 6-azido-6-deoxy-3-O-benzyl-2-O-triisopropylsilyl-β-D-glucopyranoside
  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.