N-[9-[(2R,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(trityl-amino)-tetrahydro-furan-2-yl]-2-(2-phenoxy-acetylamino)-9H-purin-6-yl]-2-phenoxy-acetamide | 329316-51-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-[9-[(2R,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(trityl-amino)-tetrahydro-furan-2-yl]-2-(2-phenoxy-acetylamino)-9H-purin-6-yl]-2-phenoxy-acetamide
• 英文别名: N-[9-[(2R,4S,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-(tritylamino)oxolan-2-yl]-2-[(2-phenoxyacetyl)amino]purin-6-yl]-2-phenoxyacetamide
• CAS: 329316-51-0
• 化学式: C₅₁H₅₅N₇O₆Si
• 分子量: 890.126
• InChiKey: LHYNRPGMDLFTNH-BBOINUFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.12
• 重原子数：
  65.0
• 可旋转键数：
  17.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  150.75
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  N-[9-[(2R,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(trityl-amino)-tetrahydro-furan-2-yl]-2-(2-phenoxy-acetylamino)-9H-purin-6-yl]-2-phenoxy-acetamide 在 二异丙基铵盐四氮唑 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 Diisopropyl-phosphoramidous acid (2S,3S,5R)-5-[2,6-bis-(2-phenoxy-acetylamino)-purin-9-yl]-3-(trityl-amino)-tetrahydro-furan-2-ylmethyl ester 2-cyano-ethyl 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：

  齐多夫定 在 palladium on activated charcoal 4-二甲氨基吡啶 、 N,O-双三甲硅基乙酰胺 、 四丁基氟化铵 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 6.75h， 生成 N-[9-[(2R,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(trityl-amino)-tetrahydro-furan-2-yl]-2-(2-phenoxy-acetylamino)-9H-purin-6-yl]-2-phenoxy-acetamide
  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