2(S)-[(2',3'-dideoxy-2',3'-didehydrothymidin-5'-yl)(hydroxy)phosphorylamino]-3-methylbutyric acid methyl ester triethylammonium salt | 1477790-70-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2(S)-[(2',3'-dideoxy-2',3'-didehydrothymidin-5'-yl)(hydroxy)phosphorylamino]-3-methylbutyric acid methyl ester triethylammonium salt
• 英文别名: N,N-diethylethanamine;N-[(2S)-1-methoxy-3-methyl-1-oxobutan-2-yl]-[[(2S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methoxy]phosphonamidic acid
• CAS: 1477790-70-7
• 化学式: C₆H₁₅N*C₁₆H₂₄N₃O₈P
• 分子量: 518.547
• InChiKey: GTVCXSLNCCTNGU-LQQCYJDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.55
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  147
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  司他夫定 在 吡啶 、 水 、 碘 、 三乙胺 、 三氯化磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.58h， 生成 2(S)-[(2',3'-dideoxy-2',3'-didehydrothymidin-5'-yl)(hydroxy)phosphorylamino]-3-methylbutyric acid methyl ester triethylammonium salt
  参考文献：
  名称：

  A Novel Synthesis of Antiviral Nucleoside Phosphoramidate and Thiophosphoramidate Prodrugs via NucleosideH-Phosphonamidates

  摘要：

  A novel and efficient method for the preparation of antiviral nucleoside 5'-H-phosphonamidates has been developed. The oxidization of the H-phosphonamidate intermediates with iodine and sulfur afforded nucleoside 5'-phosphoramidates and 5'-thiophosphoramidates in high yields.

  DOI：

  10.1080/15257770.2013.838262

文献信息

• A Novel Synthesis of Antiviral Nucleoside Phosphoramidate and Thiophosphoramidate Prodrugs via Nucleoside<i>H</i>-Phosphonamidates
  作者：Qi Sun、Xingjian Li、Shanshan Gong、Gang Liu、Liang Shen、Liang Peng

  DOI：10.1080/15257770.2013.838262

  日期：2013.11.2

  A novel and efficient method for the preparation of antiviral nucleoside 5'-H-phosphonamidates has been developed. The oxidization of the H-phosphonamidate intermediates with iodine and sulfur afforded nucleoside 5'-phosphoramidates and 5'-thiophosphoramidates in high yields.