methyl (2S)-2-[[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]amino]-3-phenylpropanoate | 320725-63-1

• 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: methyl (2S)-2-[[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]amino]-3-phenylpropanoate
• CAS: 320725-63-1
• 化学式: C₂₀H₂₅N₆O₇PS
• 分子量: 524.494
• InChiKey: PKOUDMLKAHMIEY-SQIMVDOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  173
• 氢给体数：
  3
• 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-phenylpropanoate 在 Oxone 作用下， 以80%的产率得到2(S)-(3-deoxy-3-azidothymidyl(hydroxy)phosphorylamino)-3-phenylpropionic 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-苯丙氨酸甲酯 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， 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-phenylpropanoate
  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