p-tolyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside | 1235137-39-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside
• CAS: 1235137-39-9
• 化学式: C₃₄H₃₄O₅S
• 分子量: 554.707
• InChiKey: DDANYPHUIFTAQM-ZDVOIXAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  p-tolyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 以95%的产率得到p-tolyl 2,3-di-O-benzyl-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：

  (((2S,3S,4S,5R,6R)-2-(p-tolylthio)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl)tris(oxy))tris(trimethylsilane) 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 生成 p-tolyl 2,3-di-O-benzyl-4,6-O-benzylidene-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