2'-deoxy-O⁶-<2-(4-nitrophenyl)ethyl>-N²-phthaloylguanosine | 199800-46-9

• 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'-deoxy-O⁶-<2-(4-nitrophenyl)ethyl>-N²-phthaloylguanosine
• 英文别名: 2-[9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-[2-(4-nitrophenyl)ethoxy]purin-2-yl]isoindole-1,3-dione
• CAS: 199800-46-9
• 化学式: C₂₆H₂₂N₆O₈
• 分子量: 546.496
• InChiKey: PGNUWDZSDRXAKM-XUVXKRRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  40.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  183.04
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2'-deoxy-O⁶-<2-(4-nitrophenyl)ethyl>-N²-phthaloylguanosine 在 吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 5-O-(4,4-二甲氧基三苯甲游基)-2-脱氧鸟苷
  参考文献：
  名称：

  Nucleotides, Part LXI, Phthaloyl Strategy: A New Concept of Oligonucleotide Synthesis

  摘要：

  A new alternative strategy of oligonucleotide synthesis was developed by use of thr phthaloyl protecting group for the exocyclic amino functions of the nucleobases (see 9 - 12). This approach combines the advantages of cheap and easily accessable monomeric building blocks (see 17 - 20), standard machine-aided oligonucleotide synthesis, and a fast deprotection protocol which is orthogonal to the cleavage procedure from the solid support. The crude oligonucleotides show high purity and require, in general, no further chromatographic purification.

  DOI：

  10.1002/(sici)1522-2675(19990407)82:4<633::aid-hlca633>3.0.co;2-u
• 作为产物：
  描述：

  2-[6-[2-(4-Nitro-phenyl)-ethoxy]-9-((2R,4S,5R)-4-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-yl]-isoindole-1,3-dione 在 吡啶 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.25h， 生成 2'-deoxy-O⁶-<2-(4-nitrophenyl)ethyl>-N²-phthaloylguanosine
  参考文献：
  名称：

  Nucleotides, Part LXI, Phthaloyl Strategy: A New Concept of Oligonucleotide Synthesis

  摘要：

  A new alternative strategy of oligonucleotide synthesis was developed by use of thr phthaloyl protecting group for the exocyclic amino functions of the nucleobases (see 9 - 12). This approach combines the advantages of cheap and easily accessable monomeric building blocks (see 17 - 20), standard machine-aided oligonucleotide synthesis, and a fast deprotection protocol which is orthogonal to the cleavage procedure from the solid support. The crude oligonucleotides show high purity and require, in general, no further chromatographic purification.

  DOI：

  10.1002/(sici)1522-2675(19990407)82:4<633::aid-hlca633>3.0.co;2-u

文献信息

• Phthaloyl Strategy—A New Approach Towards Oligodeoxyribonucleotide Synthesis
  作者：Markus Beier、Wolfgang Pfleiderer

  DOI：10.1080/07328319708006240

  日期：1997.7

  A new rapid strategy for machine-aided oligodeoxyribonucleotide synthesis has been established utilizing phthaloyl groups for protection of the heterocyclic amino functions within the phosphoramidite approach. A large number of DNA-sequences has been synthesized. Due to high purity and speed of performance this strategy offers an excellent alternative to the common used acyl approach.