Benzoic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxymethyl]-tetrahydro-furan-3-yl ester | 289680-30-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: Benzoic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxymethyl]-tetrahydro-furan-3-yl ester
• CAS: 289680-30-4
• 化学式: C₃₃H₃₈N₇O₆P
• 分子量: 659.682
• InChiKey: WMGHBHLYMZWJNH-QCJXDXANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.88
• 重原子数：
  47.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  153.72
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  Benzoic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxymethyl]-tetrahydro-furan-3-yl ester 在 四氮唑 、 ammonium hydroxide 、 苯基二硫化物 作用下， 以 乙腈 为溶剂， 生成 Thiophosphoric acid O-[(2R,3S,5R)-5-(6-amino-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl] ester O'-((S)-4-isopropenyl-cyclohex-1-enylmethyl) ester
  参考文献：
  名称：

  Nucleotide libraries as a source of biologically relevant chemical diversity: solution-phase synthesis

  摘要：

  Solution-phase parallel synthesis of nucleotide library I consisting of 150 members is reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00210-9
• 作为产物：
  描述：

  双(二异丙基氨基)(2-氰基乙氧基)膦 、 N6,3'-O-二苯甲酰基-2'-脱氧腺苷 在 四氮唑 作用下， 以 二氯甲烷 为溶剂， 生成 Benzoic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxymethyl]-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Synthetic Approaches to Nuclease-Resistant, Nonnatural Dinucleotides of Anti-Hiv Integrase Interest

  摘要：

  New, nonnatural dinucleotide 5'-monophosphates with a surrogate isonucleoside component of L-related stereochemistry, have been synthesized. Structures of the target compounds were confirmed by multinuclear NMR spectra (H-1, C-13, P-31, COSY), UV hypochromicity, FAB HRMS data and X-ray crystallography. These compounds are totally resistant to cleavage by 3'- and 5'-exonucleases. Dinucleotides of this study with a terminal L-isonucleoside component showed remarkable selectivity for inhibition of the strand transfer step of HIV-1 integrase. To the best of our knowledge, these compounds represent only the second example of this type of selectivity of inhibition of the strand transfer step.

  DOI：

  10.1080/15257770500265703