Acetic acid (2R,3S,5S)-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-{5-methyl-2-oxo-4-[(pyren-2-ylmethyl)-amino]-2H-pyrimidin-1-yl}-tetrahydro-furan-2-ylmethyl ester | 201219-81-0

• 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: Acetic acid (2R,3S,5S)-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-{5-methyl-2-oxo-4-[(pyren-2-ylmethyl)-amino]-2H-pyrimidin-1-yl}-tetrahydro-furan-2-ylmethyl ester
• 英文别名: [(2R,3S,5S)-3-[bis(4-methoxyphenyl)-phenylmethoxy]-5-[5-methyl-2-oxo-4-(pyren-2-ylmethylamino)pyrimidin-1-yl]oxolan-2-yl]methyl acetate
• CAS: 201219-81-0
• 化学式: C₅₀H₄₅N₃O₇
• 分子量: 799.923
• InChiKey: AGDAAOMVNAKDQC-BKXXXTAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  60
• 可旋转键数：
  14
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,5S)-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-{5-methyl-2-oxo-4-[(pyren-2-ylmethyl)-amino]-2H-pyrimidin-1-yl}-tetrahydro-furan-2-ylmethyl ester 在 sodium methylate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 Diisopropyl-phosphoramidous acid (2R,3S,5S)-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-{5-methyl-2-oxo-4-[(pyren-2-ylmethyl)-amino]-2H-pyrimidin-1-yl}-tetrahydro-furan-2-ylmethyl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  Targeting Chimeric alpha,beta-Oligonucleotides to the Flanks of a Stem in DNA. The Enhanced Effect of an Intercalator.

  摘要：

  3'-O-(4,4'-Dimethoxytrityl)-5-methyl-N-4-(1-pyrenylmethyl)-alpha-cytidine (7) was prepared from alpha-thymidine by the reaction of 1-pyrenylmethylamine with an appropriate protected 4-(1,2,4-triazolyl)-alpha-thymidine derivative 5. 3'-O-(4,4'-Dimethoxytrityl-alpha-thymidine (9) was synthesized by successive, 5'-O-acetylation, 3'-O-tritylation and 5'-O-deacetylation of alpha-thymidine. Phosphitylation of the 5'-hydroxy group of 7 and 9 afforded the amidites 8 and 10. These amidites and commercial beta-2'-deoxyribonucleoside-3'-phosphoramidites were used in the synthesis of chimeric ODNs with 3'-3' and 5'-5' internucleotidic phosphodiester linkages. The stability of a DNA three way junction (TWJ) was studied by observing the thermal melting when a DNA was targeted to the flanks of a hairpin. The TWJ was considerably stabilized when 7 and 9 were inserted into the junction region. The corresponding duplex obtained by deleting the hairpin, however, was destabilized on insertion of 7 and 9.

  DOI：

  10.3891/acta.chem.scand.51-1245
• 作为产物：
  描述：

  5'-O-acetyl-3'-O-(4,4'-dimethoxytrityl)-α-thymidine 在 三乙胺 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 5.0h， 生成 Acetic acid (2R,3S,5S)-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-{5-methyl-2-oxo-4-[(pyren-2-ylmethyl)-amino]-2H-pyrimidin-1-yl}-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  Targeting Chimeric alpha,beta-Oligonucleotides to the Flanks of a Stem in DNA. The Enhanced Effect of an Intercalator.

  摘要：

  3'-O-(4,4'-Dimethoxytrityl)-5-methyl-N-4-(1-pyrenylmethyl)-alpha-cytidine (7) was prepared from alpha-thymidine by the reaction of 1-pyrenylmethylamine with an appropriate protected 4-(1,2,4-triazolyl)-alpha-thymidine derivative 5. 3'-O-(4,4'-Dimethoxytrityl-alpha-thymidine (9) was synthesized by successive, 5'-O-acetylation, 3'-O-tritylation and 5'-O-deacetylation of alpha-thymidine. Phosphitylation of the 5'-hydroxy group of 7 and 9 afforded the amidites 8 and 10. These amidites and commercial beta-2'-deoxyribonucleoside-3'-phosphoramidites were used in the synthesis of chimeric ODNs with 3'-3' and 5'-5' internucleotidic phosphodiester linkages. The stability of a DNA three way junction (TWJ) was studied by observing the thermal melting when a DNA was targeted to the flanks of a hairpin. The TWJ was considerably stabilized when 7 and 9 were inserted into the junction region. The corresponding duplex obtained by deleting the hairpin, however, was destabilized on insertion of 7 and 9.

  DOI：

  10.3891/acta.chem.scand.51-1245