3'-azido-3'deoxy-5'-O{[(bis-benzyloxyphosphorylmethyl)benzyloxyphosphorylmethyl]benzyloxyphosphoryl}-N³-{1-[5-(2,2,2-trifluoroacetylamino)pentyl]}thymidine | 174571-56-3

• 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-3'deoxy-5'-O{[(bis-benzyloxyphosphorylmethyl)benzyloxyphosphorylmethyl]benzyloxyphosphoryl}-N³-{1-[5-(2,2,2-trifluoroacetylamino)pentyl]}thymidine
• 英文别名: N-[5-[3-[(2R,4S,5S)-4-azido-5-[[[bis(phenylmethoxy)phosphorylmethyl-phenylmethoxyphosphoryl]methyl-phenylmethoxyphosphoryl]oxymethyl]oxolan-2-yl]-5-methyl-2,6-dioxopyrimidin-1-yl]pentyl]-2,2,2-trifluoroacetamide
• CAS: 174571-56-3
• 化学式: C₄₇H₅₄F₃N₆O₁₂P₃
• 分子量: 1044.9
• InChiKey: PAMMCZIZVIWNME-MFOHSXNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  71.0
• 可旋转键数：
  27.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  228.45
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  3'-azido-3'deoxy-5'-O{[(bis-benzyloxyphosphorylmethyl)benzyloxyphosphorylmethyl]benzyloxyphosphoryl}-N³-{1-[5-(2,2,2-trifluoroacetylamino)pentyl]}thymidine 在 三甲基溴硅烷 、 氨 、 水 作用下， 以 甲醇 为溶剂， 生成 [[[(2S,3S,5R)-5-[3-(5-aminopentyl)-5-methyl-2,4-dioxopyrimidin-1-yl]-3-azidooxolan-2-yl]methoxy-hydroxyphosphoryl]methyl-hydroxyphosphoryl]methylphosphonic acid
  参考文献：
  名称：

  Synthesis of a non-hydrolyzable AZT-triphosphate analogue designed for the production of anti-AZT-TP antibodies

  摘要：

  An enzymatically stable analogue of AZT-triphosphate is prepared in 7 steps starting from thymidine. The thymine moiety is Functionalized at N-3 to allow the Further cross-linking to a carrier protein for subsequent immunization of rabbits in order to raise specific antibodies directed against AZT-TP. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00497-9
• 作为产物：
  描述：

  5-(三氟乙酰氨基)-1-戊醇 在 偶氮二甲酸二异丙酯 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 生成 3'-azido-3'deoxy-5'-O{[(bis-benzyloxyphosphorylmethyl)benzyloxyphosphorylmethyl]benzyloxyphosphoryl}-N³-{1-[5-(2,2,2-trifluoroacetylamino)pentyl]}thymidine
  参考文献：
  名称：

  Synthesis of Polyphosphorylated AZT Derivatives for the Development of Specific Enzyme Immunoassays

  摘要：

  The synthesis of a series of analogues of the different polyphosphorylated metabolites of AZT has been carried out. The compounds were designed in order to raise specific antibodies for the development of highly sensitive titration kits for the intracellular metabolites of AZT. The pyrophosphate moiety in AZT-DP and AZT-TP analogues is mimicked by the methylene bisphosphonate group to provide in vivo stability of the compounds. An omega-amino linker was introduced at the N-3 position on the base to allow the further anchoring of the compounds to a carrier protein before immunization, tentitatively focusing the specificity of the immune response toward the phosphate mimic moiety and the nonnatural sugar.

  DOI：

  10.1021/jo982502p