4-(benzyloxy)-8-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-ribofuranosyl]-2-{[(dimethylamino)methylene]amino}pteridin-7(8H)-one | 388609-85-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: 4-(benzyloxy)-8-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-ribofuranosyl]-2-{[(dimethylamino)methylene]amino}pteridin-7(8H)-one
• 英文别名: [(2R,3S,5R)-5-[2-(dimethylaminomethylideneamino)-7-oxo-4-phenylmethoxypteridin-8-yl]-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS: 388609-85-6
• 化学式: C₃₇H₃₆N₆O₇
• 分子量: 676.729
• InChiKey: RNCWQNOQBZBFJV-ILJQZKEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  50.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  147.33
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  4-(benzyloxy)-8-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-ribofuranosyl]-2-{[(dimethylamino)methylene]amino}pteridin-7(8H)-one 在 palladium-barium carbonate 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以97%的产率得到8-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-ribofuranosyl]-2-{[(dimethylamino)methylene]amino}pteridine-4,7(3H,8H)-dione
  参考文献：
  名称：

  Nucleotides, Part LXIX, Synthesis of Phosphoramidite Building Blocks of IsoxanthopterinN8-(2′-Deoxy-β-D-ribonucleosides): New Fluorescence Markers for Oligonucleotide Synthesis

  摘要：

  The chemical synthesis of isoxanthopterin and 6-phenylisoxanthopterin N-8-(2'-deoxy-beta -D-ribofuranosyl nucleosides) is described as well as their conversion into suitably protected 3'-phosphoramidite building blocks to be used as marker molecules for DNA synthesis. Applying the npe/npeoc (=2-(4-nitrophenyl)ethyl/[2-(4-nitrophenyl)ethoxy]carbonyl) strategy, we used the new building blocks in the preparation of oligonucleotides by an automated solid-support approach, The hybridization properties of a series of labelled oligomers were studied by UV-melting techniques. It was found that the newly synthesized markers only slightly interfered with the abilities of the labelled oligomers to form stable duplexes with complementary oligonucleotides.

  DOI：

  10.1002/1522-2675(20010815)84:8<2330::aid-hlca2330>3.0.co;2-u
• 作为产物：
  描述：

  2-amino-4-(benzyloxy)pteridin-7(8H)-one 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 3.5h， 生成 4-(benzyloxy)-8-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-ribofuranosyl]-2-{[(dimethylamino)methylene]amino}pteridin-7(8H)-one
  参考文献：
  名称：

  Nucleotides, Part LXIX, Synthesis of Phosphoramidite Building Blocks of IsoxanthopterinN8-(2′-Deoxy-β-D-ribonucleosides): New Fluorescence Markers for Oligonucleotide Synthesis

  摘要：

  The chemical synthesis of isoxanthopterin and 6-phenylisoxanthopterin N-8-(2'-deoxy-beta -D-ribofuranosyl nucleosides) is described as well as their conversion into suitably protected 3'-phosphoramidite building blocks to be used as marker molecules for DNA synthesis. Applying the npe/npeoc (=2-(4-nitrophenyl)ethyl/[2-(4-nitrophenyl)ethoxy]carbonyl) strategy, we used the new building blocks in the preparation of oligonucleotides by an automated solid-support approach, The hybridization properties of a series of labelled oligomers were studied by UV-melting techniques. It was found that the newly synthesized markers only slightly interfered with the abilities of the labelled oligomers to form stable duplexes with complementary oligonucleotides.

  DOI：

  10.1002/1522-2675(20010815)84:8<2330::aid-hlca2330>3.0.co;2-u