5-cyano-7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-4-{[(dimethylamino)-methylene]amino}-7H-pyrrolo[2,3-d]pyrimidine | 259244-23-0

• 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: 5-cyano-7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-4-{[(dimethylamino)-methylene]amino}-7H-pyrrolo[2,3-d]pyrimidine
• CAS: 259244-23-0
• 化学式: C₃₆H₃₆N₆O₅
• 分子量: 632.719
• InChiKey: NDIQITMVFOCUQI-DCMFLLSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  47.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  127.25
• 氢给体数：
  1.0
• 氢受体数：
  10.0

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 、 5-cyano-7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-4-{[(dimethylamino)-methylene]amino}-7H-pyrrolo[2,3-d]pyrimidine 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以69%的产率得到5-cyano-7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-4-{[(dimethylamino)-methylene]amino}-7H-pyrrolo[2,3-d]pyrimidine-3'-[(2-cyanoethyl)-N,N-diisopropyl-phosphoramidite]
  参考文献：
  名称：

  Incorporation of 2′-Deoxysangivamycin in DNA Duplexes: The Conversion of a Pyrrolo[2, 3-d]Pyrimidine Nitrile to a Carboxamide upon Oligonucleotide Deprotection

  摘要：

  Oligonucleotides containing 2'-deoxysangivamycin are described. The phosphoramidite of 2'-deoxytoyocamycin was prepared and used in solid-phase synthesis. Upon deprotection the pyrrolo[2,3-d]pyrimidine nitrile residues were converted to carboxamides. According to the T-m-measurements the 7-carboxamido group of the 7-deazaadenine moiety stabilizes the DNA duplex significantly.

  DOI：

  10.1080/07328319908044635
• 作为产物：
  描述：

  4-amino-5-cyano-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 在 吡啶 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 5-cyano-7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-4-{[(dimethylamino)-methylene]amino}-7H-pyrrolo[2,3-d]pyrimidine
  参考文献：
  名称：

  Incorporation of 2′-Deoxysangivamycin in DNA Duplexes: The Conversion of a Pyrrolo[2, 3-d]Pyrimidine Nitrile to a Carboxamide upon Oligonucleotide Deprotection

  摘要：

  Oligonucleotides containing 2'-deoxysangivamycin are described. The phosphoramidite of 2'-deoxytoyocamycin was prepared and used in solid-phase synthesis. Upon deprotection the pyrrolo[2,3-d]pyrimidine nitrile residues were converted to carboxamides. According to the T-m-measurements the 7-carboxamido group of the 7-deazaadenine moiety stabilizes the DNA duplex significantly.

  DOI：

  10.1080/07328319908044635