8-[3,5-bis-O-(4-chlorobenzoyl)-2-deoxy-β-D-ribofuranosyl]-2-(methylsulfonyl)-4-[2-(4-nitrophenyl)ethoxy]pteridin-7(8H)-one | 186293-32-3

• 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: 8-[3,5-bis-O-(4-chlorobenzoyl)-2-deoxy-β-D-ribofuranosyl]-2-(methylsulfonyl)-4-[2-(4-nitrophenyl)ethoxy]pteridin-7(8H)-one
• CAS: 186293-32-3
• 化学式: C₃₄H₂₇Cl₂N₅O₁₁S
• 分子量: 784.587
• InChiKey: DKSCDMXCIRPAAI-ZRRKCSAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  53.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  209.01
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  8-[3,5-bis-O-(4-chlorobenzoyl)-2-deoxy-β-D-ribofuranosyl]-2-(methylsulfonyl)-4-[2-(4-nitrophenyl)ethoxy]pteridin-7(8H)-one 在 氨 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到2-amino-8-[3,5-bis-O-(4-chlorobenzoyl)-2-deoxy-β-D-ribofuranosyl]-4-[2-(4-nitrophenyl)ethoxy]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
• 作为产物：
  描述：

  2-(methylthio)pteridine-4,7(3H,8H)-dione 在 偶氮二甲酸二异丙酯 、 二甲基二环氧乙烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 5.0h， 生成 8-[3,5-bis-O-(4-chlorobenzoyl)-2-deoxy-β-D-ribofuranosyl]-2-(methylsulfonyl)-4-[2-(4-nitrophenyl)ethoxy]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

文献信息

• Synthesis of 8-(2-Deoxy-β-D-Ribofuranosyl)-Isoxanthopterins New Fluorescent Analogs of 2′-Deoxyguanosine
  作者：Jörg Lehbauer、Wolfgang Pfleidere

  DOI：10.1080/07328319708002965

  日期：1997.5

  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.