7-(2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl)-1,7-dihydro-4-[(2-methylpropanoyl)amino]-2H-pyrrolo[2,3-d]pyrimidin-2-one | 227950-63-2

• 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: 7-(2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl)-1,7-dihydro-4-[(2-methylpropanoyl)amino]-2H-pyrrolo[2,3-d]pyrimidin-2-one
• 英文别名: N-[7-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-2-oxo-3H-pyrrolo[2,3-d]pyrimidin-4-yl]-2-methylpropanamide
• CAS: 227950-63-2
• 化学式: C₃₆H₃₈N₄O₇
• 分子量: 638.72
• InChiKey: FCDBXUAZKSUUIE-OJDZSJEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  47
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  三乙基碳酸氢铵缓冲液 、 7-(2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl)-1,7-dihydro-4-[(2-methylpropanoyl)amino]-2H-pyrrolo[2,3-d]pyrimidin-2-one 在 N-甲基吗啉 、 1H-1,2,4-三唑 、 三氯化磷 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 以70%的产率得到7-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-1,7-dihydro-4-[(2-methylpropanoyl)amino]-2H-pyrrolo[2,3-d]pyrimidin-2-one 3'-triethylammonium phosphonate
  参考文献：
  名称：

  The Base-Pairing Properties of 7-Deaza-2′-deoxyisoguanosine and 2′-Deoxyisoguanosine in Oligonucleotide Duplexes with Parallel and Antiparallel Chain Orientation

  摘要：

  Oligonucleotides with parallel (ps) or antiparallel (aps) chain orientation containing 7-deaza-2'-deoxyisoguanosine (1) or 2'-deoxyisoguanosine (2) were prepared. The phosphoramidite and phosphonate building blocks 3-6 were synthesized and used in solid-phase synthesis. The diphenylcarbamoyl (dpc) residue was used for the 2-oxo group protection and the isobutyryl (iBu = ib) residue fur the amino function. Hybridization experiments were performed with oligonucleotides containing 7-deazaisoguanine or isoguanine. Regarding 7-deazapurine-containing oligonucleotides, the 7-deazaisoguanine cytosine base pair was the strongest in ps-duplexes, while that of 7-deazaisoguanine.5-methylisocytosine was the most stable one in aps-DNA. Ambiguous base pairing of 7-deazaisoguanine with cytosine, 5-methylisocytosine, thymine, and guanine was observed in the case of aps-duplexes, whereas in ps-duplexes, the ambiguity was extended to adenine. The 7-deazaisoguanine-containing duplexes showed almost identical base-pair stabilities as those containing isoguanine. According to this, various base-pair motifs are proposed. The 7-deaza-2'-deoxyisoguanosine was found to be an effective substitute of 2'-deoxyisoguanosine.

  DOI：

  10.1002/(sici)1522-2675(19990505)82:5<726::aid-hlca726>3.0.co;2-k
• 作为产物：
  描述：

  (2R,3S,5R)-5-(2-amino-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate 在 吡啶 、 三甲基氯硅烷 、 氨 、 水 、 溶剂黄146 、 N,N-二异丙基乙胺 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 吡啶 、 水 为溶剂， 反应 79.83h， 生成 7-(2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl)-1,7-dihydro-4-[(2-methylpropanoyl)amino]-2H-pyrrolo[2,3-d]pyrimidin-2-one
  参考文献：
  名称：

  The Base-Pairing Properties of 7-Deaza-2′-deoxyisoguanosine and 2′-Deoxyisoguanosine in Oligonucleotide Duplexes with Parallel and Antiparallel Chain Orientation

  摘要：

  Oligonucleotides with parallel (ps) or antiparallel (aps) chain orientation containing 7-deaza-2'-deoxyisoguanosine (1) or 2'-deoxyisoguanosine (2) were prepared. The phosphoramidite and phosphonate building blocks 3-6 were synthesized and used in solid-phase synthesis. The diphenylcarbamoyl (dpc) residue was used for the 2-oxo group protection and the isobutyryl (iBu = ib) residue fur the amino function. Hybridization experiments were performed with oligonucleotides containing 7-deazaisoguanine or isoguanine. Regarding 7-deazapurine-containing oligonucleotides, the 7-deazaisoguanine cytosine base pair was the strongest in ps-duplexes, while that of 7-deazaisoguanine.5-methylisocytosine was the most stable one in aps-DNA. Ambiguous base pairing of 7-deazaisoguanine with cytosine, 5-methylisocytosine, thymine, and guanine was observed in the case of aps-duplexes, whereas in ps-duplexes, the ambiguity was extended to adenine. The 7-deazaisoguanine-containing duplexes showed almost identical base-pair stabilities as those containing isoguanine. According to this, various base-pair motifs are proposed. The 7-deaza-2'-deoxyisoguanosine was found to be an effective substitute of 2'-deoxyisoguanosine.

  DOI：

  10.1002/(sici)1522-2675(19990505)82:5<726::aid-hlca726>3.0.co;2-k