2,3,5-tri-O-pentanoyl-1-O-(1-naphthyl)-α-D-ribofuranoside | 1604045-22-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 2,3,5-tri-O-pentanoyl-1-O-(1-naphthyl)-α-D-ribofuranoside
• CAS: 1604045-22-8
• 化学式: C₃₀H₄₀O₈
• 分子量: 528.643
• InChiKey: QRDFGBQTWYDWGV-MCILKKLMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.88
• 重原子数：
  38.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-pentanoyl-1-O-(1-naphthyl)-α-D-ribofuranoside 在 甲醇 、 氨 作用下， 生成 (2R,3S,4R,5R)-2-(hydroxymethyl)-5-naphthalen-1-yloxyoxolane-3,4-diol
  参考文献：
  名称：

  Effect of acyl chain length on selective biocatalytic deacylation on O-aryl glycosides and separation of anomers

  摘要：

  It has been demonstrated that Lipozyme (R) TL IM (Thermomyces lanuginosus lipase immobilised on silica) can selectively deacylate the ester function involving the C-5' hydroxyl group of alpha-anomers over the other acyl functions of anomeric mixture of peracylated O-aryl alpha,beta-D-ribofuranoside. The analysis of results of biocatalytic deacylation reaction revealed that the reaction time decreases with the increase in the acyl chain length from C-1 to C-4. The unique selectivity of Lipozyme (R) TL IM has been harnessed for the separation of anomeric mixture of peracylated O-aryl alpha,beta-D-ribofuranosides, The lipase mediated selective deacylation methodology has been used for the synthesis of O-aryl alpha-D-ribofuranosides and O-aryl beta-D-ribofuranosides in pure forms, which can be used as chromogenic substrate for the detection of pathogenic microbial parasites containing glycosidases. (C) 2014 Published by Elsevier Inc.

  DOI：

  10.1016/j.bioorg.2014.02.004
• 作为产物：
  描述：

  2,3,5-tri-O-pentanoyl-1-O-(1-naphthyl)-D-ribofuranoside 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 异丙醚 、 正丁醇 为溶剂， 反应 3.0h， 生成 2,3,5-tri-O-pentanoyl-1-O-(1-naphthyl)-α-D-ribofuranoside
  参考文献：
  名称：

  Effect of acyl chain length on selective biocatalytic deacylation on O-aryl glycosides and separation of anomers

  摘要：

  It has been demonstrated that Lipozyme (R) TL IM (Thermomyces lanuginosus lipase immobilised on silica) can selectively deacylate the ester function involving the C-5' hydroxyl group of alpha-anomers over the other acyl functions of anomeric mixture of peracylated O-aryl alpha,beta-D-ribofuranoside. The analysis of results of biocatalytic deacylation reaction revealed that the reaction time decreases with the increase in the acyl chain length from C-1 to C-4. The unique selectivity of Lipozyme (R) TL IM has been harnessed for the separation of anomeric mixture of peracylated O-aryl alpha,beta-D-ribofuranosides, The lipase mediated selective deacylation methodology has been used for the synthesis of O-aryl alpha-D-ribofuranosides and O-aryl beta-D-ribofuranosides in pure forms, which can be used as chromogenic substrate for the detection of pathogenic microbial parasites containing glycosidases. (C) 2014 Published by Elsevier Inc.

  DOI：

  10.1016/j.bioorg.2014.02.004