1-[(4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-phenylsulfanyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione | 141192-07-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-[(4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-phenylsulfanyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione
• CAS: 141192-07-6
• 化学式: C₃₁H₃₄N₂O₄SSi
• 分子量: 558.773
• InChiKey: WVIMQXSXRPKIGV-QZIBZCQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  39.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  73.32
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  Acetic acid (4S,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-phenylsulfanyl-tetrahydro-furan-2-yl ester 、 2,4-二(三甲硅氧基)嘧啶 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到1-[(4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-phenylsulfanyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of 2',3'-Didehydro-2',3'-dideoxynucleosides Utilizing Coupling Reactions between Nucleic Bases and Phenylthio-substituted 2,3-Dideoxyribose

  摘要：

  Stereoselectivities in coupling reactions between silylated pyrimidine bases and 3- or 2-alpha-phenylthio-2,3-dideoxyribose were examined. In the former case, no stereoselectivies were observed when the coupling reactions were performed either with 1-chlorosugar in an S(N)2 mode or in the presence of Lewis acids as catalyst in an S(N)1 mode. Coupling reaction with 2-alpha-phenylthio-2,3-dideoxyribose in the presence of Lewis acids, especially SnCl4, proceeded with good stereoselectivity to give anomeric mixtures of alpha:beta = 1:9. All these nucleosides were converted to 2',3'-didehydro-2',3'-dideoxynucleosides by oxidation to sulfoxides followed by thermal elimination of sulfenic acid.

  DOI：

  10.3987/com-91-5884