Benzoic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-{(2-chloro-phenoxy)-[phenyl-(2-trityloxy-ethyl)-amino]-phosphoryloxymethyl}-tetrahydro-furan-3-yl ester | 109875-65-2

• 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: Benzoic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-{(2-chloro-phenoxy)-[phenyl-(2-trityloxy-ethyl)-amino]-phosphoryloxymethyl}-tetrahydro-furan-3-yl ester
• 英文别名: [(2R,3S,5R)-5-(6-benzamidopurin-9-yl)-2-[[(2-chlorophenoxy)-[N-(2-trityloxyethyl)anilino]phosphoryl]oxymethyl]oxolan-3-yl] benzoate
• CAS: 109875-65-2
• 化学式: C₅₇H₄₈ClN₆O₈P
• 分子量: 1011.47
• InChiKey: KIXUATAQJQBENN-WREAOIKPSA-N

物化性质

• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.96
• 重原子数：
  73.0
• 可旋转键数：
  19.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  156.23
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  N-trityloxyethylaniline 生成 Benzoic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-{(2-chloro-phenoxy)-[phenyl-(2-trityloxy-ethyl)-amino]-phosphoryloxymethyl}-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  TANAKA, TOSHIKI;YAMADA, YASUKI;IKEHARA, MORIO, CHEM. AND PHARM. BULL., 35,(1987) N 7, 2726-2733

  摘要：

  DOI：

文献信息

• Chemical synthesis of deoxyribonucleotide with a 5'-phosphoryl group on a polystyrene polymer support by the phosphotriester method.
  作者：TOSHIKI TANAKA、YASUKI YAMADA、MORIO IKEHARA

  DOI：10.1248/cpb.35.2726

  日期：——

  Highly lipophilic amines [trityloxyethylamine (TEAm) and N-trityloxyethylaniline (TEAn)] were introduced onto a 5'-phosphoryl group and the stability of the phosphoramidate linkage to acid was studied at the diester level. It was found that the phosphoramidate linkage using TEAn was cleaved by 80% aqueous acetic acid within 1 h at room temperature. However, it required 2 h to remove TEAm from the phosphate. By using the TEAn group, 5'-phosphorylated pentadecadeoxyribonucleotide pTCCAGGGTCTGGTAC was synthesized on a polystyrene support by the phosphotriester method. After partial deblocking, the pentadecamer with the TEAn group could be easily isolated on a reversed-phase column due to the high lipophilicity of the TEAn group. The chemically synthesized 5 '-phosphorylated pentadecamer was successfully joined by using deoxyribonucleic acid ligase in the presence of a template.

  高度脂溶性的胺类化合物 [三苯氧乙胺 (TEAm) 和 N-三苯氧乙基苯胺 (TEAn)] 被引入到 5' - 磷酸基团上，并研究了磷酰胺链接对酸的稳定性。在二酯水平上进行的研究发现，使用 TEAn 的磷酰胺链接在室温下可以在 1 小时内被 80% 水合醋酸切断。然而，从磷酸中去除 TEAm 需时 2 小时。通过使用 TEAn 基团，在聚苯乙烯支架上采用磷三酯法合成了 5' - 磷酸化的十五核脱氧核糖核酸 pTCCAGGGTCTGGTAC。经过部分去阻断后，具有 TEAn 基团的十五聚核苷酸由于 TEAn 基团的高脂溶性，可以在反相色谱柱上轻松分离。该化学合成的 5' - 磷酸化十五聚核苷酸成功地在模板存在下通过脱氧核糖核酸连接酶连接。
• TANAKA, TOSHIKI;YAMADA, YASUKI;TAMATSUKURI, SHIGERU;SAKATA, TAKESHI;IKEHA+, 14TH SYMP. NUCL. ACIDS CHEM., TOKUSHIMA, OCT. 30TH - NOV. 1ST, 1986, OXFO+
  作者：TANAKA, TOSHIKI、YAMADA, YASUKI、TAMATSUKURI, SHIGERU、SAKATA, TAKESHI、IKEHA+

  DOI：——

  日期：——