N⁴-{[4-(tert-butyl)phenoxy]acetyl}-2'-deoxy-3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}cytidine | 298699-72-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: N⁴-{[4-(tert-butyl)phenoxy]acetyl}-2'-deoxy-3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}cytidine
• 英文别名: N4-((4-tertbutylphenoxy)acetyl)-3'-O-[2-(2-nitrophenyl)propoxycarbonyl]-2'-deoxycytidine；[(2R,3S,5R)-5-[4-[[2-(4-tert-butylphenoxy)acetyl]amino]-2-oxopyrimidin-1-yl]-2-(hydroxymethyl)oxolan-3-yl] 2-(2-nitrophenyl)propyl carbonate
• CAS: 298699-72-6
• 化学式: C₃₁H₃₆N₄O₁₀
• 分子量: 624.648
• InChiKey: OJYXONQMUUDOMB-LPEOMECSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  45
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  182
• 氢给体数：
  2
• 氢受体数：
  10

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 、 N⁴-{[4-(tert-butyl)phenoxy]acetyl}-2'-deoxy-3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}cytidine 在 吡啶盐酸盐 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以81%的产率得到N⁴-{[4-(tert-butyl)phenoxy]acetyl}-2'-deoxy-3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}cytidine 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 N⁴-{[4-(tert-butyl)phenoxy]acetyl}-2'-deoxy-3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}cytidine
  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

• Nucleoside derivatives with photo-unstable protective groups
  申请人：Deutsches Krebsforschungszentrum Stiftund des Offentlichen Rechts

  公开号：US06756492B1

  公开（公告）日：2004-06-29

  The present invention relates to nucleoside derivatives having photolabile protective groups of general formula (I) in which R1=H, NO2, CN, OCH3, halogen, an alkyl, alkoxy or alkoxyalkyl residue having 1 to 4 C atoms or an optionally substituted aryl residue or an aliphatic acyl residue having 2 to 5 atoms, R2=H, NO2, CN, OCH3, halogen, an alkyl, alkoxy or alkoxyalkyl residue having 1 to 4 C atoms or an optionally substituted aryl residue or an aliphatic acyl residue having 2 to 5 atoms, R3=H, halogen, NO2, CN, OCH3, an alkyl, alkoxy or alkoxyalkyl residue having 1 to 4 C atoms or an optionally substituted aryl residue or aliphatic acyl residue having 2 to 5 C atoms, R4=H, halogen, NO2, CN, OCH3, an alkyl, alkoxy, or alkoxyalkyl residue having 1 to 4 C atoms or an optionally substituted aryl residue or aliphatic acyl residue having 2 to 5 atoms, R5=H, dimethoxytrityl or a protective group common in the chemistry of nucleotides or a functional group common for the production of oligonucleotides, R6=H, OH, halogen, or &PSgr;R8, wherein &PSgr;=O or S and R8=alkyl or alkoxyalkyl having 1 to 4 C atoms or an optionally substituted aryl residue or an aliphatic acyl residue having 2 to 5 atoms and a protective group common in the chemistry of nucleotides, R7=H, NO2, CN, OCH3, halogen, an alkyl, alkoxy or alkoxyalkyl residue having 1 to 4 C atoms or an optionally substituted aryl residue or aliphatic acyl residue having 2 to 5 atoms, n =0 or 1, X =SO2, OCO, OCS, B=H, adenine, cytosine, guanine, thymine, uracil, 2,6-diaminopurine-9-yl, hypoxanthine-9-yl, 5-methylcytosine-1-yl, 5-amino-4-imidazole carboxylic acid-1-yl or 5-amino-4-imidazole carboxylic acid amide-3-yl, wherein in case B=adenine, cytosine or guanine the primary amino function optionally has a temporary or permanent protective group and/or thymine or uracil optionally has a permanent protective group at the O4 position. The invention also relates to a method of producing these nucleosides, their use and nucleic acid chips built up therefrom.

  本发明涉及具有光敏保护基的核苷衍生物，其一般式为(I)，其中R1＝H、NO2、CN、OCH3、卤素、具有1至4个C原子的烷基、烷氧基或烷氧基烷基残基，或者是可选取代的芳基残基或具有2至5个原子的脂肪族酰基残基；R2＝H、NO2、CN、OCH3、卤素、具有1至4个C原子的烷基、烷氧基或烷氧基烷基残基，或者是可选取代的芳基残基或具有2至5个原子的脂肪族酰基残基；R3＝H、卤素、NO2、CN、OCH3、具有1至4个C原子的烷基、烷氧基或烷氧基烷基残基，或者是可选取代的芳基残基或具有2至5个C原子的脂肪族酰基残基；R4＝H、卤素、NO2、CN、OCH3、具有1至4个C原子的烷基、烷氧基或烷氧基烷基残基，或者是可选取代的芳基残基或具有2至5个原子的脂肪族酰基残基；R5＝H、二甲氧基三苄基基或在核苷酸化学中常见的保护基或用于寡核苷酸生产的常见功能基；R6＝H、OH、卤素或&PSgr;R8，其中&PSgr;＝O或S，R8＝具有1至4个C原子的烷基或烷氧基烷基，或者是可选取代的芳基残基或具有2至5个原子的脂肪族酰基残基和在核苷酸化学中常见的保护基；R7＝H、NO2、CN、OCH3、卤素、具有1至4个C原子的烷基、烷氧基或烷氧基烷基残基，或者是可选取代的芳基残基或具有2至5个原子的脂肪族酰基残基；n＝0或1；X＝SO2、OCO、OCS；B＝H、腺嘌呤、胞嘧啶、鸟嘌呤、胸腺嘧啶、尿嘧啶、2,6-二氨基嘌呤-9-基、次黄嘌呤-9-基、5-甲基胞嘧啶-1-基、5-氨基-4-咪唑羧酸-1-基或5-氨基-4-咪唑羧酸酰胺-3-基，在B＝腺嘌呤、胞嘧啶或鸟嘌呤的情况下，原始氨基功能可选具有临时或永久的保护基，或者胸腺嘧啶或尿嘧啶可选在O4位置具有永久的保护基。本发明还涉及一种制备这些核苷的方法、它们的用途和由此构建的核酸芯片。
• 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.