N⁶-{[4-(tert-butyl)phenoxy]acetyl}-2'-deoxy-3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}adenosine | 298699-73-7

• 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: N⁶-{[4-(tert-butyl)phenoxy]acetyl}-2'-deoxy-3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}adenosine
• 英文别名: [(2R,3S,5R)-5-[6-[[2-(4-tert-butylphenoxy)acetyl]amino]purin-9-yl]-2-(hydroxymethyl)oxolan-3-yl] 2-(2-nitrophenyl)propyl carbonate
• CAS: 298699-73-7
• 化学式: C₃₂H₃₆N₆O₉
• 分子量: 648.673
• InChiKey: RXXXJYQORYSSDI-IIEJJZGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  47
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  193
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  双(二异丙基氨基)(2-氰基乙氧基)膦 、 N⁶-{[4-(tert-butyl)phenoxy]acetyl}-2'-deoxy-3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}adenosine 在 吡啶盐酸盐 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以65%的产率得到N⁶-{[4-(tert-butyl)phenoxy]acetyl}-2'-deoxy-3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}adenosine 5'-(2-cyanoethyl diisopropylphosphoramidite)
  参考文献：
  名称：

  Synthesis of Photolabile 5′-O-Phosphoramidites for the Photolithographic Production of Microarrays of Inversely Oriented Oligonucleotides

  摘要：

  The photolabile 3 ' -O-{[2-(2-nitrophenyl)propoxy]carbonyl}-protected 5 ' -phosphoramidites (16-18) were synthesized (see Scheme) for an alternative mode of light-directed production of oligonucleotide arrays. Because of the characteristics of these monomeric building blocks, photolithographic in situ DNA synthesis occurred in 5 ' --> 3 ' direction, in agreement with the orientation of enzymatic synthesis. Synthesis yields were as good as those of conventional reactions. The resulting oligonucleotides are attached to the: surface via their 5 ' -termini, while the 3 ' -hydroxy groups are available as substrates for enzymatic reactions such as primer extension upon hybridization of a DNA template (see Fig. 2). The production of such oligonucleotide chips adds new procedural avenues to the growing number of applications of DNA microarrays.

  DOI：

  10.1002/1522-2675(20010711)84:7<2089::aid-hlca2089>3.0.co;2-0
• 作为产物：
  描述：

  1-(2-nitrophenyl)ethyl carbonochloridate 在 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 N⁶-{[4-(tert-butyl)phenoxy]acetyl}-2'-deoxy-3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}adenosine
  参考文献：
  名称：

  Synthesis of Photolabile 5′-O-Phosphoramidites for the Photolithographic Production of Microarrays of Inversely Oriented Oligonucleotides

  摘要：

  The photolabile 3 ' -O-{[2-(2-nitrophenyl)propoxy]carbonyl}-protected 5 ' -phosphoramidites (16-18) were synthesized (see Scheme) for an alternative mode of light-directed production of oligonucleotide arrays. Because of the characteristics of these monomeric building blocks, photolithographic in situ DNA synthesis occurred in 5 ' --> 3 ' direction, in agreement with the orientation of enzymatic synthesis. Synthesis yields were as good as those of conventional reactions. The resulting oligonucleotides are attached to the: surface via their 5 ' -termini, while the 3 ' -hydroxy groups are available as substrates for enzymatic reactions such as primer extension upon hybridization of a DNA template (see Fig. 2). The production of such oligonucleotide chips adds new procedural avenues to the growing number of applications of DNA microarrays.

  DOI：

  10.1002/1522-2675(20010711)84:7<2089::aid-hlca2089>3.0.co;2-0

文献信息

• Nucleosid-Derivate mit photolabilen Schutzgruppen
  申请人：Deutsches Krebsforschungszentrum Stiftung des öffentlichen Rechts

  公开号：EP1212338B1

  公开（公告）日：2012-11-21
• US6756492B1
  申请人：——

  公开号：US6756492B1

  公开（公告）日：2004-06-29
• Synthesis of Photolabile 5′-O-Phosphoramidites for the Photolithographic Production of Microarrays of Inversely Oriented Oligonucleotides
  作者：Markus Beier、Achim Stephan、Jörg D. Hoheisel

  DOI：10.1002/1522-2675(20010711)84:7<2089::aid-hlca2089>3.0.co;2-0

  日期：2001.7.11

  The photolabile 3 ' -O-[2-(2-nitrophenyl)propoxy]carbonyl}-protected 5 ' -phosphoramidites (16-18) were synthesized (see Scheme) for an alternative mode of light-directed production of oligonucleotide arrays. Because of the characteristics of these monomeric building blocks, photolithographic in situ DNA synthesis occurred in 5 ' --> 3 ' direction, in agreement with the orientation of enzymatic synthesis. Synthesis yields were as good as those of conventional reactions. The resulting oligonucleotides are attached to the: surface via their 5 ' -termini, while the 3 ' -hydroxy groups are available as substrates for enzymatic reactions such as primer extension upon hybridization of a DNA template (see Fig. 2). The production of such oligonucleotide chips adds new procedural avenues to the growing number of applications of DNA microarrays.