2-(trifluoroacetamido)-6-<(pentafluorophenyl)oxy>-9-<5-O-(4,4'-dimethoxytrityl)-2-deoxy-β-D-erythro-pentofuranosyl>purine | 145052-23-9

• 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: 2-(trifluoroacetamido)-6-<(pentafluorophenyl)oxy>-9-<5-O-(4,4'-dimethoxytrityl)-2-deoxy-β-D-erythro-pentofuranosyl>purine
• 英文别名: N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-6-(2,3,4,5,6-pentafluorophenoxy)purin-2-yl]-2,2,2-trifluoroacetamide
• CAS: 145052-23-9
• 化学式: C₃₉H₂₉F₈N₅O₇
• 分子量: 831.676
• InChiKey: VHCURGGLAAKVDL-JIMJEQGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  59
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  139
• 氢给体数：
  2
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  2-(trifluoroacetamido)-6-<(pentafluorophenyl)oxy>-9-<5-O-(4,4'-dimethoxytrityl)-2-deoxy-β-D-erythro-pentofuranosyl>purine 在 N-甲基吗啉 、 1H-1,2,3-三氮唑 、 三氯化磷 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以65%的产率得到2-(trifluoroacetamido)-6-<(pentafluorophenyl)oxy>-9-<5-O-(4,4'-dimethoxytrityl)-2-deoxy-3-O-(H-phosphonyl)-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
• 作为产物：
  描述：

  4,4'-双甲氧基三苯甲基氯 、 2-N-trifluoroacetamido-6-pentafluorophenoxy-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine 在 吡啶 作用下， 反应 20.0h， 以95%的产率得到2-(trifluoroacetamido)-6-<(pentafluorophenyl)oxy>-9-<5-O-(4,4'-dimethoxytrityl)-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

文献信息

• 6-O-(Pentafluorophenyl)-2'-deoxyguanosine: a versatile synthon for nucleoside and oligonucleotide synthesis
  作者：Hetian Gao、Reza Fathi、Barbara L. Gaffney、Bhaswati Goswami、Pei Pei Kung、Youngsook Rhee、Renzhe Jin、Roger A. Jones

  DOI：10.1021/jo00051a051

  日期：1992.12

  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.