3'-O-acetyl-2'-deoxy-α-D-thymidine | 52474-37-0

• 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: 3'-O-acetyl-2'-deoxy-α-D-thymidine
• 英文别名: 3’-O-acetyl-thymidine；3'-O-acetyl-α-thymidine；3'-O-Acetyl-α-thymidin；1-(O³-acetyl-α-D-erythro-2-deoxy-pentofuranosyl)-5-methyl-1H-pyrimidine-2,4-dione；[(2R,3S,5S)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate
• CAS: 52474-37-0
• 化学式: C₁₂H₁₆N₂O₆
• 分子量: 284.269
• InChiKey: IRFKBRPHBYCMQU-AEJSXWLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.94
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  110.62
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ammonium O-ethyl [4-(methoxycarbonyl)phenylaminocarbonyl]methylphosphonate 、 3'-O-acetyl-2'-deoxy-α-D-thymidine 在 吡啶 、 N,N'-二环己基碳二亚胺 作用下， 反应 12.0h， 以90%的产率得到O-ethyl O'-(3'-O-acetyl-α-D-thymidine-5'-yl) [4-(methoxycarbonyl)phenylaminocarbonyl]methylphosphonate
  参考文献：
  名称：

  Synthesis and biological properties of α-thymidine 5′-aryl phosphonates

  摘要：

  Diethyl(N-arylaminocarbonyl)methyl phosphonates have been obtained by the reaction of diethylphosphonoacetic acid imidazolides with methyl-4-aminobenzoate or 3,5-bis(trifluoromethyl)phenylamine. Their treatment with Me3SiBr in DMF led to a mixture of the corresponding (N-arylaminocarbonylmethyl)phosphonic acids and their monoethyl esters. After separation, they were condensed with 3'-O-acetyl-alpha-thymidine, which, after the removal of the acetyl protecting group, gave (alpha-D-thymidine-5'-yl)-[4-aminocarbonyl-, methoxycarbonyl-, or carboxy)phenylaminocarbonyl]methyl phosphonates and (alpha-D-thymidine-5'-yl)-[3,5-bis(trifluoromethyl)phenylaminocarbonyl]methyl phosphonate and their ethyl esters. It was shown that the compounds are stable under different conditions, low toxic (in Vero and K-562 cell cultures), and capable of penetrating into K-562 cells. Only ethyl (alpha-D-thymidine-5'-yl)-[4-(methoxycarbonyl)phenylaminocarbonyl]methyl phosphonate at a high concentration (200 mu g/mL) inhibited in vitro the growth of the laboratory strain M. tuberculosis H37Rv.

  DOI：

  10.1134/s1068162013060058
• 作为产物：
  描述：

  (2R,3S,5R)-2-((((2-(benzyl(piperidin-2-ylmethyl)amino)ethoxy)carbonyl)oxy)methyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl acetate 以 aq. phosphate buffer 、 乙腈 为溶剂， 生成 2-苄基八氢-1H-吡啶并[1,2-a]吡嗪 、 3'-O-acetyl-2'-deoxy-α-D-thymidine
  参考文献：
  名称：

  [EN] OLIGONUCLEOTIDE AND NUCLEIC ACID SYNTHESIS
  [FR] SYNTHÈSE D'OLIGONUCLÉOTIDES ET D'ACIDES NUCLÉIQUES

  摘要：

  公开号：

  WO2019145713A9