phenyl 2-O-tert-butyldimethylsilyl-3-O-benzyl-4,6-di-O-acetyl-β-D-glucopyranoside | 566197-63-5

• 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-4,6-di-O-acetyl-β-D-glucopyranoside
• CAS: 566197-63-5
• 化学式: C₂₉H₄₀O₈Si
• 分子量: 544.717
• InChiKey: BULIGDYRAFDGJF-RKFAPSRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.26
• 重原子数：
  38.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  phenyl 2-O-tert-butyldimethylsilyl-3-O-benzyl-4,6-di-O-acetyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 (2R,3R,4S,5R,6S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-6-phenoxy-tetrahydro-pyran-3-ol
  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：

  乙酸酐 、 (2R,3R,4S,5R,6S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-6-phenoxy-tetrahydro-pyran-3-ol 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以24 mg的产率得到phenyl 2-O-tert-butyldimethylsilyl-3-O-benzyl-4,6-di-O-acetyl-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