4-Methyl-benzoic acid (2S,3R,4R,5R)-4-acetoxy-3-azido-5-[2,6-bis-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-2-ylmethyl ester | 256485-51-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 4-Methyl-benzoic acid (2S,3R,4R,5R)-4-acetoxy-3-azido-5-[2,6-bis-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-2-ylmethyl ester
• CAS: 256485-51-5
• 化学式: C₃₆H₃₃N₉O₉
• 分子量: 735.713
• InChiKey: ZDHVCEIAYPFFSJ-SXXUQIFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  54.0
• 可旋转键数：
  14.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  230.85
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  4-Methyl-benzoic acid (2S,3R,4R,5R)-4-acetoxy-3-azido-5-[2,6-bis-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-2-ylmethyl ester 在 咪唑 、 N-甲基咪唑 、 sodium hydroxide 作用下， 以 吡啶 、 甲醇 、 水 为溶剂， 反应 93.12h， 生成 4-Methoxy-benzoic acid (2S,3R,4R,5R)-5-[2,6-bis-(2-phenoxy-acetylamino)-purin-9-yl]-4-(tert-butyl-dimethyl-silanyloxy)-3-{[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  A Remarkable Stabilization of Complexes Formed by 2,6-Diaminopurine Oligonucleotide N3′→P5′ Phosphoramidates

  摘要：

  2'-Deoxyribo- and ribo-oligonucleotide N3'-->P5' phosphoramidates containing 2,6-diaminopurine nucleosides were synthesized. Thermal denaturation experiments demonstrated a significant stabilization of the complexes formed by these compounds with DNA and RNA complementary strands, relative to adenosine-containing phosphoramidate counterparts. The increase in melting temperature of the complexes reached up to 6.9 degreesC per substitution. The observed stabilization was attributed to the apparent synergistic effects of M-type sugar puckering of the oligonucleotide N3'-->P5' phosphoramidate backbone, and the ability of 2,6-diaminopurine bases to form three hydrogen bonds.

  DOI：

  10.1080/15257770008045446
• 作为产物：
  描述：

  3-azido-1,2-di-O-acetyl-5-O-(p-toluoyl)-3-deoxy-D-ribofuranose 、 N²,N⁶-bis(phenoxyacetyl)-N²,N⁶,9-tris(trimethylsilyl)-2,6-diaminopurine 在 三氟甲磺酸三甲基硅酯 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以3.52 g的产率得到4-Methyl-benzoic acid (2S,3R,4R,5R)-4-acetoxy-3-azido-5-[2,6-bis-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  A Remarkable Stabilization of Complexes Formed by 2,6-Diaminopurine Oligonucleotide N3′→P5′ Phosphoramidates

  摘要：

  2'-Deoxyribo- and ribo-oligonucleotide N3'-->P5' phosphoramidates containing 2,6-diaminopurine nucleosides were synthesized. Thermal denaturation experiments demonstrated a significant stabilization of the complexes formed by these compounds with DNA and RNA complementary strands, relative to adenosine-containing phosphoramidate counterparts. The increase in melting temperature of the complexes reached up to 6.9 degreesC per substitution. The observed stabilization was attributed to the apparent synergistic effects of M-type sugar puckering of the oligonucleotide N3'-->P5' phosphoramidate backbone, and the ability of 2,6-diaminopurine bases to form three hydrogen bonds.

  DOI：

  10.1080/15257770008045446