3-azido-2',3'-dideoxythymidine 5'-fluorophosphate | 156497-10-8

• 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-azido-2',3'-dideoxythymidine 5'-fluorophosphate
• 英文别名: 3'-azido-3'-deoxythymidin-5'-yl) phosphoromonofluoridate；3'-azido-3'-deoxythymidine 5'-phosphorofluoridate；F-AZTMP；[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)tetrahydrofuran-2-yl]methoxy-fluoro-phosphinic acid；[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-fluorophosphinic acid
• CAS: 156497-10-8
• 化学式: C₁₀H₁₃FN₅O₆P
• 分子量: 349.215
• InChiKey: SMOCPMVULMGVPP-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3'-azido-3'-deoxythymidin-5'-yl) O-(4-nitrophenyl) N,N-diisopropylphosphoramidite 在 叔丁基过氧化氢 、 三甲基氯硅烷 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 4.17h， 生成 3-azido-2',3'-dideoxythymidine 5'-fluorophosphate
  参考文献：
  名称：

  Synthesis of phosphorofluoridates and phosphorofluoridothioates via the phosphoramidite approach

  摘要：

  我们介绍了一种非常高效的合成方法，能够制备出磷氟酸盐RO-P(O)(OH)F 1或磷氟硫酸盐RO-P(S)(OH)F 2，其方法基于氟磷酰胺中间体(RO)P(F)NiPr25 [R = 9-(羟乙氧甲基)鸟嘌呤基、3′叠氮-3′脱氧胸苷基、胸苷基、脱水胸苷基、胆固醇基、N6-苯甲酰-5′-O-(4,4′-二甲氧基三苯甲基)-2′-脱氧腺苷基]。氨基的活化采用三甲基氯硅烷（TMCS）完成。

  DOI：

  10.1039/b413552k

文献信息

• Synthesis and Antiviral Activity of Some Fluorinated Nucleotide Derivatives
  作者：Natalia Dyatkina、Andrey Arzumanov、Alexander Krayevsky、Bryan O'Hara、Yacov Gluzman、Penny Baron、Clarinda MacLow、Bruce Polsky

  DOI：10.1080/15257779408013244

  日期：1994.3

  A number of 3'-fluoro-3'-deoxythymidine 5'-phosphonates and nucleoside 5'-phosphorofluoridates were prepared to study their ability to inhibit replication of HIV-1. Compounds, the 5'-phosphorofluoridates of 3'-azido-3'-deoxythymidine (VIIIc), 3'-fluoro-3'-deoxythymidine (VIIId) and 3'-deoxy-2',3'-didehydrothymidine (VIIIe), exhibit potent anti-HTV-1 activities.
• Synthesis of phosphorofluoridates and phosphorofluoridothioates via the phosphoramidite approach
  作者：Wojciech Dabkowski、Izabela Tworowska

  DOI：10.1039/b413552k

  日期：——

  We present a very efficient synthetic procedure leading to the phosphorofluoridates RO-P(O)(OH)F 1 or phosphorofluoridothioates RO-P(S)(OH)F 2, which is based on the intermediary of fluorophosphoramidites (RO)P(F)NiPr25 [R = 9-(hydroxyethyloxymethyl)guaninyl), 3′azido-3′deoxythymidinyl, thymidinyl, anhydrothymidinyl, cholesteryl, N6-benzoyl-5′-O-(4,4′-dimethoxytrityl)-2′-deoxyadenosinyl]. The activation of the amino group was performed with trimethylchlorosilane (TMCS).

  我们介绍了一种非常高效的合成方法，能够制备出磷氟酸盐RO-P(O)(OH)F 1或磷氟硫酸盐RO-P(S)(OH)F 2，其方法基于氟磷酰胺中间体(RO)P(F)NiPr25 [R = 9-(羟乙氧甲基)鸟嘌呤基、3′叠氮-3′脱氧胸苷基、胸苷基、脱水胸苷基、胆固醇基、N6-苯甲酰-5′-O-(4,4′-二甲氧基三苯甲基)-2′-脱氧腺苷基]。氨基的活化采用三甲基氯硅烷（TMCS）完成。