Acetic acid (2R,3S,5S)-2-azidomethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester | 158603-56-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 2 '，5'-二脱氧核苷
• 英文名称: Acetic acid (2R,3S,5S)-2-azidomethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
• CAS: 158603-56-6
• 化学式: C₁₂H₁₅N₅O₅
• 分子量: 309.282
• InChiKey: WSGCZIPIFONUNE-AEJSXWLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.37
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  139.15
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,5S)-2-azidomethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 在 氨 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以76%的产率得到1-(5-azido-2,5-dideoxy-α-D-erythro-pentofuranosyl)thymine
  参考文献：
  名称：

  5'-Azido and 5'-Fluoro alpha-Nucleosides as Analogues of AZT and FLT.

  摘要：

  5-Azido-2,5-dideoxy-beta-D-erythro-pentofuranosyl nucleosides 10 and their corresponding alpha-anomers 11 have been synthesized by condensation of methyl 3-O-acetyl-5-azido-2,5-dideoxy-beta-D-erythro-pentofuranoside (7) with silylated nucleobases followed by deprotection with methanolic ammonia. Reaction of silylated thymine (19) with methyl 2,3-di-O-benzoyl-5-deoxy-5-fluoro-D-arabino-pentofuranoside (15) and methyl 5-azido-2,3-di-O-benzoyl-5-deoxy-alpha-D-arabino-pentofuranoside (17alpha) afforded a mixture of the alpha-nucleosides 20 and the acyclo nucleosides 5-fluoro- and 5-azido-2,3-O-dibenzoyl-5-deoxy-1-O-methyl-1-(thymin-1-yl)-D-arabinitol (22). Compounds 20 and 22 were deprotected with methanolic ammonia to give the acyclic nucleosides 21 and 23, respectively. The new nucleosides were inactive against HSV-1 and HIV-1.

  DOI：

  10.3891/acta.chem.scand.48-0215
• 作为产物：
  描述：

  methyl 2-deoxy-5-O-(p-toluenesulfonyl)-β-D-erythro-pentofuranoside 在 吡啶 、 sodium azide 、 三氟甲磺酸三甲基硅酯 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 54.5h， 生成 Acetic acid (2R,3S,5S)-2-azidomethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  5'-Azido and 5'-Fluoro alpha-Nucleosides as Analogues of AZT and FLT.

  摘要：

  5-Azido-2,5-dideoxy-beta-D-erythro-pentofuranosyl nucleosides 10 and their corresponding alpha-anomers 11 have been synthesized by condensation of methyl 3-O-acetyl-5-azido-2,5-dideoxy-beta-D-erythro-pentofuranoside (7) with silylated nucleobases followed by deprotection with methanolic ammonia. Reaction of silylated thymine (19) with methyl 2,3-di-O-benzoyl-5-deoxy-5-fluoro-D-arabino-pentofuranoside (15) and methyl 5-azido-2,3-di-O-benzoyl-5-deoxy-alpha-D-arabino-pentofuranoside (17alpha) afforded a mixture of the alpha-nucleosides 20 and the acyclo nucleosides 5-fluoro- and 5-azido-2,3-O-dibenzoyl-5-deoxy-1-O-methyl-1-(thymin-1-yl)-D-arabinitol (22). Compounds 20 and 22 were deprotected with methanolic ammonia to give the acyclic nucleosides 21 and 23, respectively. The new nucleosides were inactive against HSV-1 and HIV-1.

  DOI：

  10.3891/acta.chem.scand.48-0215