Benzoic acid (2R,3S)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-3-benzenesulfinyl-tetrahydro-furan-2-ylmethyl ester | 146455-22-3

• 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: Benzoic acid (2R,3S)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-3-benzenesulfinyl-tetrahydro-furan-2-ylmethyl ester
• CAS: 146455-22-3
• 化学式: C₂₄H₂₃N₃O₆S
• 分子量: 481.529
• InChiKey: HRVNEZQBUSKBFR-OMTGKLIKSA-N

反应信息

• 作为反应物：
  描述：

  Benzoic acid (2R,3S)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-3-benzenesulfinyl-tetrahydro-furan-2-ylmethyl ester 在 4-甲基吡啶 作用下， 以 xylene 为溶剂， 反应 4.0h， 生成 N⁴-acetyl-1-(5-O-benzoyl-2,3-dideoxy-α-D-glycero-pento-2-enofuranosyl)cytosine 、 N⁴-acetyl-1-(5-O-benzoyl-2,3-dideoxy-β-D-glycero-pento-2-enofuranosyl)cytosine
  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
• 作为产物：
  描述：

  N⁴-acetyl-(5-O-benzoyl-2,3-dideoxy-3-phenylthio-D-erythro-pentofuranosyl)cytosine 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 Benzoic acid (2R,3S)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-3-benzenesulfinyl-tetrahydro-furan-2-ylmethyl ester
  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