p-tolyl 4,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranoside | 1320281-35-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl 4,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranoside
• CAS: 1320281-35-3
• 化学式: C₂₄H₂₇N₃O₆S
• 分子量: 485.561
• InChiKey: SXYXRZJGWDBZRR-HUUMMWPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  119.82
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  p-tolyl 4,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranoside 在 甲醇 、 sodium methylate 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 96.0h， 生成 p-tolyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Mannopyranosyl Uronic Acid Donor Reactivity

  摘要：

  The reactivity of a variety of mannopyranosyl uronic acid donors was assessed In a set of competition experiments, in which two (S)-tolyl mannosyl donors were made to compete for a limited amount of promoter (NIS/TfOH). These experiments revealed that the reactivity of mannuronic acid donors is significantly higher than expected based on the electron-withdrawing capacity of the C-5 carboxylic acid ester function. A 4-O-acetyl-beta-(S)-tolyl mannuronic acid donor was found to have similar reactivity as per-O-benzyl-alpha-(S)-tolyl mannose.

  DOI：

  10.1021/ol2016862
• 作为产物：
  描述：

  acetyl 4,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-D-mannopyranoside 、 4-甲苯硫酚 在 三氟化硼乙醚 作用下， 以 1,1-二氯乙烷 为溶剂， 反应 2.0h， 以41%的产率得到p-tolyl 4,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Mannopyranosyl Uronic Acid Donor Reactivity

  摘要：

  The reactivity of a variety of mannopyranosyl uronic acid donors was assessed In a set of competition experiments, in which two (S)-tolyl mannosyl donors were made to compete for a limited amount of promoter (NIS/TfOH). These experiments revealed that the reactivity of mannuronic acid donors is significantly higher than expected based on the electron-withdrawing capacity of the C-5 carboxylic acid ester function. A 4-O-acetyl-beta-(S)-tolyl mannuronic acid donor was found to have similar reactivity as per-O-benzyl-alpha-(S)-tolyl mannose.

  DOI：

  10.1021/ol2016862