methyl (p-tolyl 4-O-acetyl-2,3-di-O-benzyl-1-thio-α-D-mannopyranosyl uronate) | 1320281-32-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (p-tolyl 4-O-acetyl-2,3-di-O-benzyl-1-thio-α-D-mannopyranosyl uronate)
• 英文别名: methyl (2S,3S,4S,5S,6R)-3-acetyloxy-6-(4-methylphenyl)sulfanyl-4,5-bis(phenylmethoxy)oxane-2-carboxylate
• CAS: 1320281-32-0
• 化学式: C₃₀H₃₂O₇S
• 分子量: 536.646
• InChiKey: ICJWMWGCSVJVIY-LOLMJFKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 、 methyl (p-tolyl 4-O-acetyl-2,3-di-O-benzyl-1-thio-α-D-mannopyranosyl uronate) 、 p-tolyl 4,6-di-O-acetyl-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以55%的产率得到methyl 2,3,4-tri-O-benzyl-6-O-(4,6-di-O-acetyl-2,3-di-O-benzyl-α/β-D-mannopyranosyl)-α-D-glucopyranoside
  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：

  p-methylphenyl 2,3-di-O-benzyl-1-thio-α-D-mannopyranoside 在 吡啶 、 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (p-tolyl 4-O-acetyl-2,3-di-O-benzyl-1-thio-α-D-mannopyranosyl uronate)
  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