8-[3,5-bis-O-(4-chlorobenzoyl)-2-deoxy-β-D-ribofuranosyl]-2-(methylthio)-6-phenylpteridine-4,7(3H,8H)-dione | 195821-80-8

• 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: 8-[3,5-bis-O-(4-chlorobenzoyl)-2-deoxy-β-D-ribofuranosyl]-2-(methylthio)-6-phenylpteridine-4,7(3H,8H)-dione
• CAS: 195821-80-8
• 化学式: C₃₂H₂₄Cl₂N₄O₇S
• 分子量: 679.537
• InChiKey: IXRNBCWUKCROIC-RBZQAINGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.55
• 重原子数：
  46.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  142.47
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  8-[3,5-bis-O-(4-chlorobenzoyl)-2-deoxy-β-D-ribofuranosyl]-2-(methylthio)-6-phenylpteridine-4,7(3H,8H)-dione 在 氰化钠 、 氨 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 2-amino-8-[2-deoxy-β-D-ribofuranosyl]-4-[2-(4-nitrophenyl)ethoxy]-6-phenylpteridin-7(8H)-one
  参考文献：
  名称：

  Synthesis of 8-(2-Deoxy-β-D-Ribofuranosyl)-Isoxanthopterins New Fluorescent Analogs of 2′-Deoxyguanosine

  摘要：

  We have synthesized isoxanthopterin and 6-phenylisoxanthopterin nucleosides in form of their 5'-O-dimethoxytritylated 3'-phosphoramidites to be used as fluorescence markers directly in the synthesis of oligonucleotides by a machine-aided solid-support approach. The preparation of the monomers and some results of the oligonucleotide synthesis will be described.

  DOI：

  10.1080/07328319708002965
• 作为产物：
  描述：

  6-amino-5-[(2-methoxy-2-oxo-1-phenylethylidene)amino]-2-(methylthio)pyrimidin-4(3H)-one 在 吡啶 、 sodium hydroxide 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 1.92h， 生成 8-[3,5-bis-O-(4-chlorobenzoyl)-2-deoxy-β-D-ribofuranosyl]-2-(methylthio)-6-phenylpteridine-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