2'-O-pentanoyl-5'-O-(4,4'-dimethoxytrityl)-2',3'-secouridine | 1416449-90-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2'-O-pentanoyl-5'-O-(4,4'-dimethoxytrityl)-2',3'-secouridine
• CAS: 1416449-90-5
• 化学式: C₃₅H₄₀N₂O₉
• 分子量: 632.711
• InChiKey: TZFRLVCQJOAPHR-XDFJSJKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  46.0
• 可旋转键数：
  17.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  138.31
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  戊酸酐 、 5'-O-(4,4'-dimethoxytrityl)-2',3'-secouridine 在 Theremomyces lanuginosus lipase immobilized on silica 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以58%的产率得到2'-O-pentanoyl-5'-O-(4,4'-dimethoxytrityl)-2',3'-secouridine
  参考文献：
  名称：

  Selective Biocatalytic Acylation Studies on 5′-O-(4,4′-Dimethoxytrityl)-2′,3′-Secouridine: An Efficient Synthesis of UNA Monomer

  摘要：

  Lipozyme (R) TL IM (Theremomyces lanuginosus lipase immobilized on silica) in toluene catalyzes the acylation of the 2 '-OH over the 3 '-OH group in 5 '-O-(4,4 '-dimethoxytrityl)-2 ',3 '-secouridine (5 '-O-DMT-2 ',3 '-secouridine) in a highly selective fashion in moderate to almost quantitative yields. The turn over during benzoyl transfer reactions mediated by vinyl benzoate or benzoic anhydride was faster than in acyl transfer reactions with vinyl acetate or C1 to C5 acid anhydrides; except in the case of butanoic anhydride. The 2 '-O-benzoyl-5 '-O-DMT-2 ',3 '-secouridine obtained by Lipozyme (R) TL IM catalyzed benzoylation of 5 '-O-DMT-2 ',3 '-secouridine was successfully converted into its 3 '-O-phosphoramidite derivative in satisfactory yield, which is a building block for the preparation of oligonucleotides containing the uracil monomer of UNA (unlocked nucleic acid).

  DOI：

  10.1080/15257770.2012.734424