3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}thymidine | 298699-71-5

• 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: 3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}thymidine
• 英文别名: thymidine 3'-[2-(2-nitrophenyl)propyl carbonate]；3'-O-[2-(2-nitrophenyl)propoxycarbonyl]thymidine；[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] 2-(2-nitrophenyl)propyl carbonate
• CAS: 298699-71-5
• 化学式: C₂₀H₂₃N₃O₉
• 分子量: 449.417
• InChiKey: ANVKJBSWPJROCX-GUPZPADCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  160
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}thymidine 在 isopropyl thioxanthone 作用下， 以 乙腈 为溶剂， 生成 1-硝基-2-丙-1-烯-2-基苯 、 beta-胸苷
  参考文献：
  名称：

  敏化双光子光化学脱保护。

  摘要：

  可光除去的保护基NPPOc对双光子激发几乎不敏感，限制了其在需要对其光化学进行高度空间控制的应用中的用途。但是，在存在具有大的两个光子吸收截面的三重态敏化剂的情况下，将两个光子解开作用的截面提高到可用于多种应用的水平。

  DOI：

  10.1039/c0cc00782j
• 作为产物：
  描述：

  硝基乙苯 生成 3'-O-{[2-(2-nitrophenyl)propoxy]carbonyl}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

• 一种碳酸酯类光敏试剂及其制备方法、5`-光敏保护核苷的制备方法
  申请人：石平

  公开号：CN105968016A

  公开（公告）日：2016-09-28

  本发明涉及一种碳酸酯类光敏试剂及其制备方法、5'‑光敏保护核苷的制备方法。碳酸酯类光敏试剂，其结构式为：其中X为-OX’、咪唑基、取代咪唑基；5'-光敏保护核苷的制备方法步骤包括将2’-脱氧核苷与2-邻硝基苯-1-丙基碳酸酯类光敏试剂和三乙胺得5'-光敏保护核苷粗产物、粗产物提纯得到5'-光敏保护核苷。本发明5'-光敏保护核苷制备方法选择性平均提高了3.4倍，减化了提纯过程，提高了产率，大大降低了生产成本，同时避免了使用剧毒的双光气。
• New Types of Very Efficient Photolabile Protecting Groups Based upon the[2-(2-Nitrophenyl)propoxy]carbonyl (NPPOC) Moiety
  作者：Sigrid Bühler、Irene Lagoja、Heiner Giegrich、Klaus-Peter Stengele、Wolfgang Pfleiderer

  DOI：10.1002/hlca.200490060

  日期：2004.3

  in a broad range depending on the substituents. So far, the thymidine 5′-[2-(5-halo-2-nitrophenyl)propyl carbonates] 127–129, 5′-[2-(nitro[1,1′-biphenyl]3-yl)propyl carbonates] 136–139, 5′-2-[2-nitro-5-(thianthren-1-yl)phenyl]propyl carbonate} (140), 5′-[2-(5-naphthalenyl-2-nitrophenyl)propyl carbonates] 141 and 142, and 5′-[2-(2-nitro-5-thienylphenyl)propyl carbonates] 143 and 144 showed the best

  基于光不稳定的[2-（2-硝基苯基）丙氧基]羰基（NPPOC），大量修饰的2-（2-硝基苯基）丙醇衍生物在苯环上被取代（参见23 – 34和57 – 76），以及在侧链上（见85 – 92和95 – 98）被合成以改善这种新型的光不稳定实体的光反应性。苯基部分也被萘基（请参阅102、103、105、108、110、113和114），噻吩基取代基（请参阅115、117、118和120）和苯并噻吩基取代基（请参见115、117、118和113）进行交换。121）。的2-（2- nitroaryl-和杂芳基）丙醇转化用双光气成相应carbonochloridates，其与胸苷随后反应胸苷5' - （被保护的碳酸酯）123 - 178作为主要的反应产物。在某些情况下，相应的3'-碳酸酯和3'，5'-二碳酸酯179 – 212也被分离出来并进行了表征。在标准条件下的光解研究（见表）表明，光裂解的速率
• 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。
• Multimer polynucleotide synthesis
  申请人：——

  公开号：US20040203036A1

  公开（公告）日：2004-10-14

  The present invention relates to a process for the preparation of polynucleotides, whereby under suitable usual conditions the free 5′-hydroxy group, whose terminal 3′-hydroxy group contains a usual protecting group, is reacted with a hydroxy group, derivatized in a previous reaction step to a phosphite amidoester, phosphpotriester or phosphonic acid ester, whereby said hydroxy group is a 3′-hydroxy function of a free or solid phase bound polynucleotide, or a solid phase bound hydroxy function. Further the present invention relates to a kit for performing a process according to the invention, which contains at least one or more selected oligonucleotides, having a free 5′-hydroxy group and a protected 3′-hydroxy group. Further on, the present invention relates to new oligonucleotides and their use as building blocks for the synthesis of polynucleotides in the process according to the invention. Furthermore the present invention relates to the use of the process according to the invention or the use of the kits for the preparation of poly/oligonucleotides resp. polynucleotide libraries or nucleic acid chips.

  本发明涉及一种制备多核苷酸的工艺，在适当的通常条件下，游离的5′-羟基（其末端3′-羟基含有通常的保护基团）与羟基反应、在前一反应步骤中衍生为亚磷酸酰胺酯、亚磷酸三酯或膦酸酯，其中所述羟基是游离的或固相结合的多核苷酸的 3′-羟基官能团，或固相结合的羟基官能团。 本发明还涉及一种用于实施本发明工艺的试剂盒，该试剂盒含有至少一种或多种选定的寡核苷酸，这些寡核苷酸具有游离的 5′-羟基和受保护的 3′-羟基。此外，本发明还涉及新的寡核苷酸及其在根据本发明的工艺中作为合成多核苷酸的构件的用途。 此外，本发明还涉及根据本发明的工艺或试剂盒在制备多核苷酸/寡核苷酸以及多核苷酸文库或核酸芯片中的用途。
• 3‘-Nitrophenylpropyloxycarbonyl (NPPOC) Protecting Groups for High-Fidelity Automated 5‘ → 3‘ Photochemical DNA Synthesis
  作者：Michael C. Pirrung、Laixin Wang、Michael P. Montague-Smith

  DOI：10.1021/ol0069150

  日期：2001.4.1

  The most powerful DNA microarrays would be prepared by photolithography with free 3'-ends that could be processed enzymatically, A photoremovable group that could be removed in quantitative yield would ensure high purity of the synthesized probes. We have developed new pyrimidine building blocks for 5' - 3' DNA synthesis with high cycle yields using the NPPOC (3' nitrophenylpropyloxycarbonyl) protecting group. These phosphoramidites were proved in automated photochemical DNA synthesis on a modified synthesizer.