phenyl 2-O-tert-butyldimethylsilyl-3-O-benzyl-4-O-ethyl-6-deoxy-6-azido-β-D-glucopyranoside | 566197-65-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2-O-tert-butyldimethylsilyl-3-O-benzyl-4-O-ethyl-6-deoxy-6-azido-β-D-glucopyranoside
• CAS: 566197-65-7
• 化学式: C₂₇H₃₉N₃O₅Si
• 分子量: 513.709
• InChiKey: DYJVYPRWMZRPHW-WSGIOKLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.48
• 重原子数：
  36.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  94.91
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  phenyl 2-O-tert-butyldimethylsilyl-3-O-benzyl-4-O-ethyl-6-deoxy-6-azido-β-D-glucopyranoside 在 Lindlar's catalyst 吡啶 、 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 乙酸乙酯 为溶剂， 反应 1.0h， 生成 phenyl 3-O-benzyl-4-O-ethyl-6-deoxy-6-acetylamino-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of novel HIV-1 protease inhibitors based on carbohydrate scaffolds

  摘要：

  The synthesis of peptidomimetic inhibitors of HIV-1 protease based on 6-deoxy-6-aniino-beta-D-glucopyranoside and 6-deoxy-6-amino- beta-D-mannopyranoside scaffolds has been achieved. The inhibitors had IC50 values in the micromolar range. The results provide a platform for the development of more potent carbohydrate based inhibitors of HIV-1 and other aspartic proteases. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00208-4
• 作为产物：
  描述：

  phenyl 2-O-tert-butyldimethylsilyl-3-O-benzyl-6-O-tosyl-β-D-glucopyranoside 在 sodium azide 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 phenyl 2-O-tert-butyldimethylsilyl-3-O-benzyl-4-O-ethyl-6-deoxy-6-azido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of novel HIV-1 protease inhibitors based on carbohydrate scaffolds

  摘要：

  The synthesis of peptidomimetic inhibitors of HIV-1 protease based on 6-deoxy-6-aniino-beta-D-glucopyranoside and 6-deoxy-6-amino- beta-D-mannopyranoside scaffolds has been achieved. The inhibitors had IC50 values in the micromolar range. The results provide a platform for the development of more potent carbohydrate based inhibitors of HIV-1 and other aspartic proteases. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00208-4