methyl 2,4-di-O-acetyl-3-O-benzyl-6-deoxy-6-acetylamino-β-D-glucopyranoside | 566197-67-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,4-di-O-acetyl-3-O-benzyl-6-deoxy-6-acetylamino-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-2-(acetamidomethyl)-5-acetyloxy-6-methoxy-4-phenylmethoxyoxan-3-yl] acetate
• CAS: 566197-67-9
• 化学式: C₂₀H₂₇NO₈
• 分子量: 409.436
• InChiKey: MOHNSCBRVPWNIL-OUUBHVDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.94
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  109.39
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 2,4-di-O-acetyl-3-O-benzyl-6-deoxy-6-acetylamino-β-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 反应 16.0h， 以100%的产率得到methyl 3-O-benzyl-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：

  methyl 3-O-benzyl-6-O-tosyl-β-D-glucopyranoside 在 吡啶 、 sodium azide 、 三苯基膦 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成 methyl 2,4-di-O-acetyl-3-O-benzyl-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