phenyl 3,4-di-O-acetyl-2-deoxy-2-phthalimido-6-O-(N-phenylcarbamoyl)-1-thio-β-D-glucopyranoside | 1449790-68-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3,4-di-O-acetyl-2-deoxy-2-phthalimido-6-O-(N-phenylcarbamoyl)-1-thio-β-D-glucopyranoside
• CAS: 1449790-68-4
• 化学式: C₃₁H₂₈N₂O₉S
• 分子量: 604.637
• InChiKey: OPSDGQSINHSPPL-YFQBHRANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  43.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  137.54
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  phenyl 3,4-di-O-acetyl-2-deoxy-2-phthalimido-6-O-(N-phenylcarbamoyl)-1-thio-β-D-glucopyranoside 在 吡啶 、 二碳酸二叔丁酯 、 四丁基亚硝酸铵 作用下， 反应 4.0h， 以70%的产率得到phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Selective Deprotection Method of N-Phenylcarbamoyl Group

  摘要：

  We report an improved method for the selective deprotection of the N-phenylcarbamoyl group, which yields the corresponding alcohol without affecting other protecting groups. Deprotection was performed using di-tert-butyl dicarbonate and tetra-n-butylammonium nitrite (Boc(2)O and Bu4NNO2) in pyridine at room temperature. This method is also effective for deprotecting the fluorous N-phenylcarbamoyl group.

  DOI：

  10.1021/jo4007128
• 作为产物：
  描述：

  phenyl-3,4-di-O-acetyl-2-phthalimido-2-deoxy-1-thio-β-D-glucopyranoside 、 异氰酸苯酯 在 吡啶 作用下， 反应 3.0h， 以95%的产率得到phenyl 3,4-di-O-acetyl-2-deoxy-2-phthalimido-6-O-(N-phenylcarbamoyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Selective Deprotection Method of N-Phenylcarbamoyl Group

  摘要：

  We report an improved method for the selective deprotection of the N-phenylcarbamoyl group, which yields the corresponding alcohol without affecting other protecting groups. Deprotection was performed using di-tert-butyl dicarbonate and tetra-n-butylammonium nitrite (Boc(2)O and Bu4NNO2) in pyridine at room temperature. This method is also effective for deprotecting the fluorous N-phenylcarbamoyl group.

  DOI：

  10.1021/jo4007128