methyl (2S)-2-[[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]amino]-3-(1H-indol-3-yl)propanoate | 320725-64-2

• 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: methyl (2S)-2-[[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]amino]-3-(1H-indol-3-yl)propanoate
• CAS: 320725-64-2
• 化学式: C₂₂H₂₆N₇O₇PS
• 分子量: 563.531
• InChiKey: JWOCZRMCDSXOCE-GYTSIINFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  189
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]amino]-3-(1H-indol-3-yl)propanoate 在 Oxone 作用下， 以82%的产率得到2(S)-(hydroxy(3-deoxy-3-azidothymidyl)phosphorylamino)-3-(3-indolyl)propionic acid methyl ester
  参考文献：
  名称：

  Conjugation of amino acid O-methyl esters with AZT-5′-O-phosphorothioate and phosphorodithioate

  摘要：

  Based upon 1,3,2-oxathia(-dithia)phospholane chemistry, 5'-O-derivatisation of AZT with the O-methyl esters of L-phenylalanine and L-tryptophan was performed and the corresponding 5'-aminoacidophosphoramidothioates or phosphoramidodithioates of AZT were obtained in satisfactory yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01635-x
• 作为产物：
  描述：

  L-色氨酸甲酯 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 吡啶 、 乙腈 为溶剂， 反应 3.0h， 生成 methyl (2S)-2-[[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]amino]-3-(1H-indol-3-yl)propanoate
  参考文献：
  名称：

  Conjugation of amino acid O-methyl esters with AZT-5′-O-phosphorothioate and phosphorodithioate

  摘要：

  Based upon 1,3,2-oxathia(-dithia)phospholane chemistry, 5'-O-derivatisation of AZT with the O-methyl esters of L-phenylalanine and L-tryptophan was performed and the corresponding 5'-aminoacidophosphoramidothioates or phosphoramidodithioates of AZT were obtained in satisfactory yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01635-x