Acetic acid (2R,3S,4R,6S)-3-acetoxy-2-acetoxymethyl-6-(2-hydroxy-naphthalen-1-yl)-tetrahydro-pyran-4-yl ester | 142061-25-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Acetic acid (2R,3S,4R,6S)-3-acetoxy-2-acetoxymethyl-6-(2-hydroxy-naphthalen-1-yl)-tetrahydro-pyran-4-yl ester
• 英文别名: 1-(3',4',6'-tri-O-acetyl-2'-deoxy-β-D-arabino-hexopyranosyl)naphthalen-2-ol
• CAS: 142061-25-4；142061-30-1
• 化学式: C₂₂H₂₄O₈
• 分子量: 416.428
• InChiKey: PFERNSJUXWAGDV-HIUFNZKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  108.36
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  2-萘酚 、 1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 在 三氟甲磺酸三甲基硅酯 、 silver perchlorate 作用下， 以 二氯甲烷 为溶剂， 生成 1-(3',4',6'-tri-O-acetyl-2'-deoxy-β-D-arabino-hexopyranosyl)naphthalen-2-ol 、 Acetic acid (2R,3S,4R,6S)-3-acetoxy-2-acetoxymethyl-6-(2-hydroxy-naphthalen-1-yl)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Efficient C-arylglycosylation of 1-O-methyl sugar by novel use of TMSOTf-AgClO4 catalyst system

  摘要：

  Highly beta-stereoselective C-arylglycosylations of the 1-O-methyl sugars 1 approximately 4 with 2-naphthol (9) were effectively achieved by novel combinational use of a catalytic amount of TMSOTf-AgClO4 as an activator. Also, C-arylglycosylations of the 1-O-acetyl sugars 5 approximately 8 with 9 in this way worked as well.

  DOI：

  10.1016/0040-4039(92)88170-a