{2-[(2R,3S,5R)-3-叠氮-5-(5-甲基-2,4-二羰基-3,4-二氢嘧啶-1(2H)-基)四氢呋喃-2-基]乙基}膦酸 | 124685-20-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: {2-[(2R,3S,5R)-3-叠氮-5-(5-甲基-2,4-二羰基-3,4-二氢嘧啶-1(2H)-基)四氢呋喃-2-基]乙基}膦酸
• 英文名称: 6'-<(3'-azido-2',3',5',6'-tetradeoxy-β-D-ribo-hexofuranosyl)-1-thymine>-phosphonic acid
• 英文别名: (2R,4S,5R)-1-<4-azidotetrahydro-5-(2-phosphonoethyl)-2-furyl>thymine；3',5'-Dideoxy-5'-phosphonomethyl-3'-azido-thymidine；2-[(2R,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]ethylphosphonic acid
• CAS: 124685-20-7
• 化学式: C₁₁H₁₆N₅O₆P
• 分子量: 345.252
• InChiKey: BCFAOZSYFUNSAJ-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-[(3'R,4'R)-2',5',6'-trideoxy-6'-(diethoxyphosphinyl)-β-hexofuranosyl]thymine 在 吡啶 、 叠氮化锂 、 三甲基溴硅烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 {2-[(2R,3S,5R)-3-叠氮-5-(5-甲基-2,4-二羰基-3,4-二氢嘧啶-1(2H)-基)四氢呋喃-2-基]乙基}膦酸
  参考文献：
  名称：

  糖，核苷和α-氨基酸膦酸酯的新合成。

  摘要：

  在膦酸乙烯基酯的存在下衍生自糖醛酸或α-氨基酸的N-羟基-2-硫代吡啶酮酯的光解得到相应的膦酸酯衍生物。描述了一种方便的合成AZT-5'单磷酸等位基因的途径。

  DOI：

  10.1016/s0040-4020(01)88721-4

文献信息

• Stereoselectivity in radical reactions of 2′-deoxynucleosides. A synthesis of an isostere of 3′-azido-3′-deoxythymidine-5′-monophosphate (AZT-5′ monophosphate)
  作者：Derek H.R. Barton、Stephan D. Géro、Béatrice Quiclet-Sire、Mohammad Samadi

  DOI：10.1016/s0040-4039(01)80556-6

  日期：1989.1
• 3'-Azido-3',5'-dideoxythymidine-5'-methylphosphonic acid diphosphate: synthesis and HIV-1 reverse transcriptase inhibition.
  作者：G. A. Freeman、J. L. Rideout、W. H. Miller、J. E. Reardon

  DOI：10.1021/jm00095a014

  日期：1992.8

  3'-Azido-3'-deoxythymidine-5'-phosphonate was synthesized by a five-step reaction sequence. The 5'-phosphonate was inactive against HIV-1 in MT4 cells. The absence of activity against HIV-1 was at least partially explained by demonstrating that the K(m) value for the 5-deoxy-5-methylphosphonic acid diphosphate analog with HIV-1 reverse transcriptase (RT) was 320-fold greater than the K(m) value for 3'-azido-3'-deoxythymidine-5-triphosphate (AZTTP), and the k(cat) value for the 5-deoxy-5-methylphosphonic acid diphosphate analog was one-seventh the value for AZTTP. These differences in kinetic constants were due to a change in the rate-determining step from dissociation of the RT chain-terminated template-primer complex to the catalytic step. Thus, substitution of a methylene group for the 5-oxygen atom of AZTTP resulted in an 1800-fold reduction in the rate constant for RT-catalyzed phosphodiester bond formation.
• TANAKA, HIROMICHI;FUKUI, MARIKO;HARAGUCHI, KAZUHIRO;MASAKI, MARIKO;MIYASA+, TETRAHEDRON LETT., 30,(1989) N9, C. 2567-2570
  作者：TANAKA, HIROMICHI、FUKUI, MARIKO、HARAGUCHI, KAZUHIRO、MASAKI, MARIKO、MIYASA+

  DOI：——

  日期：——
• BARTON, DEREK H. R.;GERO, STEPHAN D.;QUICLET-SIRE, BEATRICE;SAMADI, MOHAM+, TETRAHEDRON LETT., 30,(1989) N7, C. 4969-4972
  作者：BARTON, DEREK H. R.、GERO, STEPHAN D.、QUICLET-SIRE, BEATRICE、SAMADI, MOHAM+

  DOI：——

  日期：——
• New synthesis of sugar, nucleoside and α-amino acid phosphonates.
  作者：Derek H.R. Barton、Stephane D. Géro、Béatrice Quiclet-Sire、Mohammad Samadi

  DOI：10.1016/s0040-4020(01)88721-4

  日期：1992.2

  Photolysis of N-hydroxy-2-thiopyridone esters derived from uronic acids or α-amino acids in presence of vinyl phosphonate affords the corresponding phosphonate derivatives. A convenient route for the synthesis of the isostere of AZT-5′ monophosphate is described.

  在膦酸乙烯基酯的存在下衍生自糖醛酸或α-氨基酸的N-羟基-2-硫代吡啶酮酯的光解得到相应的膦酸酯衍生物。描述了一种方便的合成AZT-5'单磷酸等位基因的途径。