2-(trifluoroacetimido)-6-<4-(dimethylamino)pyridyl>-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine | 145052-26-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2-(trifluoroacetimido)-6-<4-(dimethylamino)pyridyl>-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine
• 英文别名: 2-(trifluoroacetimido)-6-[4-(dimethylamino)pyridyl]-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine；(1Z)-N-[6-[4-(dimethylamino)pyridin-1-ium-1-yl]-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-2-yl]-2,2,2-trifluoroethanimidate
• CAS: 145052-26-2
• 化学式: C₁₉H₂₀F₃N₇O₄
• 分子量: 467.408
• InChiKey: LGGVWPOOAPXSTI-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  136
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-(trifluoroacetimido)-6-<4-(dimethylamino)pyridyl>-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine 在 重水 作用下， 生成 2-amino-6-<4-(dimethylamino)pyridyl>-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine trifluoroacetate
  参考文献：
  名称：

  6-O-(Pentafluorophenyl)-2'-deoxyguanosine: a versatile synthon for nucleoside and oligonucleotide synthesis

  摘要：

  The 6-O-(pentafluorophenyl)-2-deoxyguanosine derivative 2a can be used to generate in high yield 6-O-methyl-2'-deoxyguanosine, 2,6-diamino-9-(2-deoxy-beta-D-erythro-pentofuranosyl)purine, and related derivatives. Further, after appropriate protection and derivatization, 2a can be incorporated into oligonucleotides and there used for postsynthetic oligonucleotide modification. This approach is particularly useful for preparation of oligonucleotides containing 2,6-diaminopurine residues or their 6-alkylamino derivatives. In addition, reaction of 2a or oligonucleotides containing it, with 4-(dimethylamino)pyridine (DMAP) gives a fluorescent guanine-DMAP adduct.

  DOI：

  10.1021/jo00051a051
• 作为产物：
  描述：

  4-二甲氨基吡啶 、 2-N-trifluoroacetamido-6-pentafluorophenoxy-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine 在 ammonium hydroxide 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以84%的产率得到2-(trifluoroacetimido)-6-<4-(dimethylamino)pyridyl>-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine
  参考文献：
  名称：

  6-O-(Pentafluorophenyl)-2'-deoxyguanosine: a versatile synthon for nucleoside and oligonucleotide synthesis

  摘要：

  The 6-O-(pentafluorophenyl)-2-deoxyguanosine derivative 2a can be used to generate in high yield 6-O-methyl-2'-deoxyguanosine, 2,6-diamino-9-(2-deoxy-beta-D-erythro-pentofuranosyl)purine, and related derivatives. Further, after appropriate protection and derivatization, 2a can be incorporated into oligonucleotides and there used for postsynthetic oligonucleotide modification. This approach is particularly useful for preparation of oligonucleotides containing 2,6-diaminopurine residues or their 6-alkylamino derivatives. In addition, reaction of 2a or oligonucleotides containing it, with 4-(dimethylamino)pyridine (DMAP) gives a fluorescent guanine-DMAP adduct.

  DOI：

  10.1021/jo00051a051