2-N-trifluoroacetamido-6-pentafluorophenoxy-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine | 128790-76-1

• 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-N-trifluoroacetamido-6-pentafluorophenoxy-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine
• 英文别名: (2-N-trifluoroacetamido-6-O-pentafluorophenyl)-2'-deoxyguanosine；2′-deoxy-2-trifluoroacetyl-6-O-pentafluorophenylguanosine；2,2,2-trifluoro-N-[9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(2,3,4,5,6-pentafluorophenoxy)purin-2-yl]acetamide
• CAS: 128790-76-1
• 化学式: C₁₈H₁₁F₈N₅O₅
• 分子量: 529.303
• InChiKey: KFIKWWRRRTUWEZ-KVQBGUIXSA-N

物化性质

• 密度：
  1.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  2-N-trifluoroacetamido-6-pentafluorophenoxy-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine 在 ammonium hydroxide 、 重水 作用下， 以 乙腈 为溶剂， 反应 18.0h， 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：

  2'-脱氧鸟苷 以 吡啶 为溶剂， 生成 2-N-trifluoroacetamido-6-pentafluorophenoxy-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine
  参考文献：
  名称：

  Porphyrinyl-nucleosides containing fluorinated nucleobases

  摘要：

  Porphyrins were synthesized in which a meso-p-phenylene-0- bridge joins the porphine core with 6-C of 5-fluorouridine (protected), 5-CF3-thymidine or 2-N-trifluoroacetamidato-6-0-pentafluorophenyl-2'-deoxyguanosine.

  DOI：

  10.1016/s0040-4039(00)73921-9

文献信息

• Synthesis of 6-substituted 2′-deoxyguanosine derivatives using trifluoroacetic anhydride in pyridine
  作者：Fathi Reza、Goswami Bhaswati、Kung Pei-Pei、Barbara L. Gaffney、Roger A. Jones

  DOI：10.1016/s0040-4039(00)94543-x

  日期：1990.1

  Trifluoroacetic anhydride at 0° C reacts with a pyridine suspension of deoxyguanosine to generate a polar intermediate, presumably the corresponding 6-pyridyl derivative. The reaction is complete in less than 15 minutes, and is not accompanied by degradation. From this intermediate a variety of 6-substituted deoxyguanosine derivatives can be obtained, some in excellent yields.

  0℃下的三氟乙酸酐与脱氧鸟苷的吡啶悬浮液反应，生成极性中间体，可能是相应的6-吡啶基衍生物。反应在不到15分钟的时间内完成，并且没有降解。从该中间体可以得到多种6-取代的脱氧鸟苷衍生物，其中一些具有优异的收率。