5'-O-(2-(2,6-dinitrophenyl)ethoxycarbonyl)thymidine | 179691-37-3

• 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: 5'-O-(2-(2,6-dinitrophenyl)ethoxycarbonyl)thymidine
• 英文别名: 2-(2,6-dinitrophenyl)ethyl [(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl carbonate
• CAS: 179691-37-3
• 化学式: C₁₉H₂₀N₄O₁₁
• 分子量: 480.388
• InChiKey: WDAXWOSLPFUHKF-ARFHVFGLSA-N

物化性质

• 密度：
  1.534±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  206
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2,6-二硝基甲苯 生成 5'-O-(2-(2,6-dinitrophenyl)ethoxycarbonyl)thymidine
  参考文献：
  名称：

  New Photolabile Protecting Groups in Nucleoside and Nucleotide Chemistry—Synthesis, Cleavage Mechanisms and Applications

  摘要：

  New photolabile protecting groups have been found in the 2-(2-nitrophenyl)ethoxycarbonyl and the 2-(2-nitrophenyl)ethylsulfonyl group, respectively. The influence of substituents at the phenyl ring as well as the side-chain has been investigated regarding the photolysis rates on irradiation at 365 mn. beta-Branching in the side-chain leads to highly increased rates of photodeprotection. A new type of photocleavage mechanism consisting of a photoinduced beta-elimination process is proposed.

  DOI：

  10.1080/07328319808004738

文献信息

• Nucleoside derivatives with photolabile protective groups
  申请人：Pfleiderer; Wolfgang

  公开号：US05763599A1

  公开（公告）日：1998-06-09

  The invention relates to nucleoside derivatives having photolabile protective groups of the general formula (I) ##STR1## in which R.sup.1 .dbd.H, NO.sub.2, CN, OCH.sub.3, halogen or alkyl or alkoxyalkyl having 1 to 4 C atoms R.sup.2 .dbd.H, OCH.sub.3 R.sup.3 .dbd.H, F, Cl, Br, NO.sub.2 R.sup.4 .dbd.H, halogen, OCH.sub.3, or an alkyl radical having 1 to 4 C atoms R.sup.5 .dbd.H or a usual functional group for preparing oligonucleotides R.sup.6 .dbd.H, OH, halogen or XR.sup.8, where X.dbd.O or S and R.sup.8 represents a protective group usual in nucleotide chemistry, B=adenine, cytosine, guanine, thymine, uracil, 2,6-diaminopurin-9-yl, hypoxanthin-9-yl, 5-methylcytosin-1-yl, 5-amino-4-imidazolcarboxamid-1-yl, or 5-amino-4-imidazolcarboxamid-3-yl, where in the case of B=adenine, cytosine or guanine, the primary amino function optionally exhibits a permanent protective group. These derivatives may be used for the light-controlled synthesis of oligonucleotides on a DNA chip.

  本发明涉及具有光敏保护基的核苷酸衍生物，其通式为(I)： 其中，R1 = H、NO2、CN、OCH3、卤素或具有1至4个碳原子的烷基或烷氧基烷基；R2 = H、OCH3；R3 = H、F、Cl、Br、NO2；R4 = H、卤素、OCH3或具有1至4个碳原子的烷基基团；R5 = H或用于制备寡核苷酸的常见官能团；R6 = H、OH、卤素或XR8，其中X = O或S，R8代表核苷酸化学中常见的保护基；B = 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-咪唑羧酰胺-1-基或5-氨基-4-咪唑羧酰胺-3-基，其中在B = 腺嘌呤、胞嘧啶或鸟嘌呤的情况下，原始氨基功能可以选择性地具有永久保护基。这些衍生物可用于在DNA芯片上进行光控制合成寡核苷酸。
• Photolabile protecting groups for nucleosides: Synthesis and photodeprotection rates
  作者：Ahmad Hasan、Klaus-Peter Stengele、Heiner Giegrich、Paul Cornwell、Kenneth R. Isham、Richard A. Sachleben、Wolfgang Pfleiderer、Robert S. Foote

  DOI：10.1016/s0040-4020(97)00154-3

  日期：1997.3

  o-Nitrobenzyloxycarbonyl and a number of related groups have been tested for the photolabile protection of nucleoside 5'-hydroxyls. The rates of photodeprotection were found to vary by approximately 17 fold in a series of 5'-O-protected thymidine derivatives irradiated at 365 nm under identical conditions. The homologous 2-(o-nitrophenyl)ethoxycarbonyl group and its derivatives were found to be removed approximately 2-fold faster than the corresponding o-nitrobenzyloxycarbonyl group, possibly due to an increased rare of alpha-hydrogen abstraction by the photo-excited nitro group. Photolysis rates were affected by substitutions on both the phenyl ring and alpha-carbon, with the strongest rate enhancements caused by the presence of a methyl or second o-nitrophenyl group in the alpha-position. Among the ring-substituted derivatives studied, o-nitro and o-iodo had the strongest enhancement effects on photodeprotection, while an o-fluoro group reduced the rate of photodeprotection. In general, substitutions at other positions on the phenyl ring had less effect on photolysis rates. (C) 1997 Elsevier Science Ltd.
• NUCLEOSID-DERIVATE MIT PHOTOLABILEN SCHUTZGRUPPEN
  申请人：Pfleiderer, Wolfgang

  公开号：EP0797580B1

  公开（公告）日：2002-04-10
• US5763599A
  申请人：——

  公开号：US5763599A

  公开（公告）日：1998-06-09
• New Photolabile Protecting Groups in Nucleoside and Nucleotide Chemistry—Synthesis, Cleavage Mechanisms and Applications
  作者：H. Giegrich、S. Eisele-Bühler、Chr Hermann、E. Kvasyuk、R. Charubala、W. Pfleiderer

  DOI：10.1080/07328319808004738

  日期：1998.9

  New photolabile protecting groups have been found in the 2-(2-nitrophenyl)ethoxycarbonyl and the 2-(2-nitrophenyl)ethylsulfonyl group, respectively. The influence of substituents at the phenyl ring as well as the side-chain has been investigated regarding the photolysis rates on irradiation at 365 mn. beta-Branching in the side-chain leads to highly increased rates of photodeprotection. A new type of photocleavage mechanism consisting of a photoinduced beta-elimination process is proposed.