1-[2-deoxy-3-O-(4,4'-dimethoxytrityl)-α-D-pentofuranosyl]-5-methyl-4-(4-phenoxyphenylamino)pyrimidin-2(1H)-one | 242815-23-2

• 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: 1-[2-deoxy-3-O-(4,4'-dimethoxytrityl)-α-D-pentofuranosyl]-5-methyl-4-(4-phenoxyphenylamino)pyrimidin-2(1H)-one
• 英文别名: 1-[(2S,4S,5R)-4-[bis(4-methoxyphenyl)-phenylmethoxy]-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-4-(4-phenoxyanilino)pyrimidin-2-one
• CAS: 242815-23-2
• 化学式: C₄₃H₄₁N₃O₇
• 分子量: 711.814
• InChiKey: OMLBNJOVFGECLV-UHULTCERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  53
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-氰乙基N,N-二异丙基氯亚磷酰胺 、 1-[2-deoxy-3-O-(4,4'-dimethoxytrityl)-α-D-pentofuranosyl]-5-methyl-4-(4-phenoxyphenylamino)pyrimidin-2(1H)-one 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以83%的产率得到Diisopropyl-phosphoramidous acid (2R,3S,5S)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-[5-methyl-2-oxo-4-(3-phenoxy-phenylamino)-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  Stabilizing a DNA Three-Way Junction by Insertion of N4-Aryl-2-deoxy-5-methylcytidines.

  摘要：

  4,4'-Dimethoxytrityl and acetyl sugar protected alpha and beta thymidines are converted into the corresponding N-4-aryl-2-deoxy-5-methylcytidines via 4-(2,4,6-trimethylbenzenesulfonyloxy) pyrimidin-2(1H)-one nucleosides. These compounds were used for DNA synthesis after deacetylation and phosphitylation. Increased melting temperatures (6.2-9.6 degrees C) of three-way junctions (TWJ) were observed when N-4-(2-anilinophenyl)-, N-4-(2-benzylphenyl)- or N-4-(2-fluorenyl)-2-deoxy-5-methylcytidines were inserted into the middle of the junction region. A 26.6 degrees C increase in melting temperature was observed using a nucleosides in one of the strands of TWJ and with insertion of 2-deoxy-N-4-(2-fluorenyl)-5-methyl-alpha-cytidine at the junction. A large increase in thermal melting (18.8 degrees C) of the TWJ was also observed when 2-deoxy-5-methyl-N-4-(4-phenoxyphenyl)-alpha-cytidine was inserted at the junction as a chimeric nucleoside into a strand of beta nucleosides.

  DOI：

  10.3891/acta.chem.scand.53-0497
• 作为产物：
  描述：

  1-[5-O-acetyl-2-deoxy-3-O-(4,4'-dimethoxytrityl)-α-D-pentofuranosyl]-5-methyl-4-(4-phenoxyphenylamino)pyrimidin-2(1H)-one 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以100%的产率得到1-[2-deoxy-3-O-(4,4'-dimethoxytrityl)-α-D-pentofuranosyl]-5-methyl-4-(4-phenoxyphenylamino)pyrimidin-2(1H)-one
  参考文献：
  名称：

  Stabilizing a DNA Three-Way Junction by Insertion of N4-Aryl-2-deoxy-5-methylcytidines.

  摘要：

  4,4'-Dimethoxytrityl and acetyl sugar protected alpha and beta thymidines are converted into the corresponding N-4-aryl-2-deoxy-5-methylcytidines via 4-(2,4,6-trimethylbenzenesulfonyloxy) pyrimidin-2(1H)-one nucleosides. These compounds were used for DNA synthesis after deacetylation and phosphitylation. Increased melting temperatures (6.2-9.6 degrees C) of three-way junctions (TWJ) were observed when N-4-(2-anilinophenyl)-, N-4-(2-benzylphenyl)- or N-4-(2-fluorenyl)-2-deoxy-5-methylcytidines were inserted into the middle of the junction region. A 26.6 degrees C increase in melting temperature was observed using a nucleosides in one of the strands of TWJ and with insertion of 2-deoxy-N-4-(2-fluorenyl)-5-methyl-alpha-cytidine at the junction. A large increase in thermal melting (18.8 degrees C) of the TWJ was also observed when 2-deoxy-5-methyl-N-4-(4-phenoxyphenyl)-alpha-cytidine was inserted at the junction as a chimeric nucleoside into a strand of beta nucleosides.

  DOI：

  10.3891/acta.chem.scand.53-0497