methyl 2,3,4-tri-O-benzyl-6-O-(methyl 4-O-acetyl-3-O-benzyl-2-deoxy-2-fluoro-β-D-mannopyranosyl uronate)-α-D-glucopyranoside | 1320281-68-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzyl-6-O-(methyl 4-O-acetyl-3-O-benzyl-2-deoxy-2-fluoro-β-D-mannopyranosyl uronate)-α-D-glucopyranoside
• CAS: 1320281-68-2
• 化学式: C₄₄H₄₉FO₁₂
• 分子量: 788.864
• InChiKey: NXEMMZVBNRUYBD-WSXFDQOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.88
• 重原子数：
  57.0
• 可旋转键数：
  18.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  126.44
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 、 methyl (2S,3S,4S,5S,6S)-3-acetyloxy-4,5-bis(phenylmethoxy)-6-phenylsulfanyloxane-2-carboxylate 、 methyl (phenyl 4-O-acetyl-3-O-benzyl-2-deoxy-2-fluoro-1-thio-α-D-mannopyranosyluronate) 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， 生成 methyl 2,3,4-tri-O-benzyl-6-O-(methyl (4-O-acetyl-2,3-di-O-benzyl-β-D-mannopyranosyl)uronate)-α-D-glucopyranoside 、 methyl 2,3,4-tri-O-benzyl-6-O-(methyl 4-O-acetyl-3-O-benzyl-2-deoxy-2-fluoro-β-D-mannopyranosyl uronate)-α-D-glucopyranoside 、 methyl 2,3,4-tri-O-benzyl-6-O-(methyl 4-O-acetyl-3-O-benzyl-2-deoxy-2-fluoro-α-D-mannopyranosyl uronate)-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