5'-O-[2-(2-nitrophenyl)propyl-sulfonyl]-thymidine | 199123-06-3

• 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-nitrophenyl)propyl-sulfonyl]-thymidine
• 英文别名: [(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl 2-(2-nitrophenyl)propane-1-sulfonate
• CAS: 199123-06-3
• 化学式: C₁₉H₂₃N₃O₉S
• 分子量: 469.472
• InChiKey: RXIFTVQJXGBEGF-GUPZPADCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  176
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5'-O-[2-(2-nitrophenyl)propyl-sulfonyl]-thymidine 以 甲醇 、 水 为溶剂， 反应 0.17h， 以43%的产率得到beta-胸苷
  参考文献：
  名称：

  New Photolabile Protecting Groups of the 2-(2-Nitrophenyl)ethoxycarbonyl- and the 2-(2-Nitrophenyl)ethylsulfonyl-Type for the Oligonucleotide Synthesis

  摘要：

  DOI：

  10.1080/07328319908044692
• 作为产物：
  描述：

  硝基乙苯 在 氯化亚砜 、 氯 、 sodium thiosulfate 作用下， 生成 5'-O-[2-(2-nitrophenyl)propyl-sulfonyl]-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：Wolfgang Pfleiderer

  公开号：US06153744A1

  公开（公告）日：2000-11-28

  The invention relates to nucleo-side derivatives with photo-unstable protective groups of the general formula (I) ##STR1## in which R.sup.1 is H, NO.sub.2, CN, OCH.sub.3, halogen, alkyl or alkoxyalkyl with 1 to 4 C atoms, R.sup.2 is H, OCH.sub.3, R.sup.3 is H, F, Cl, Br, NO.sub.2 or an aliphatic acyl radical with 2 to 5 C atoms, R.sup.4 is H, halogen, OCH.sub.3, an alkyl radical with 1 to 4 C atoms or a possibly substituted aryl radical, R.sup.5 is H or a conventional functional group for producing oligonucleotides, R.sup.6 is H, OH, halogen or XR.sup.8, where X is O or S and R.sup.8 is a conventional protective group in nucleotide chemistry, B is adenine, cytosin, guanine, thymine, uracil, 2,6-diaminopurin-9-yl, hypoxanthin-9-yl, 5-methylcytosin-1-yl, 5-amino-4-imidazol carboxylic acid amid-1-yl or 5-amino-4-imidazol carboxylic acid amide-3-yl, where, if B is adenine, cytosin or guanine, the primary amino function may have a permanent protective group. These derivatives may be used for the light-controlled synthesis of oligonucleotides on a DNA chip.

  本发明涉及具有光不稳定保护基的核苷衍生物，其一般式为（I）##STR1##其中，R.sup.1是H、NO.sub.2、CN、OCH.sub.3、卤素、烷基或1至4个C原子的烷氧基烷基，R.sup.2是H、OCH.sub.3，R.sup.3是H、F、Cl、Br、NO.sub.2或具有2至5个C原子的脂肪酰基基团，R.sup.4是H、卤素、OCH.sub.3、具有1至4个C原子的烷基基团或可能取代的芳基基团，R.sup.5是H或用于生产寡核苷酸的常规功能基团，R.sup.6是H、OH、卤素或XR.sup.8，其中X是O或S，R.sup.8是核苷酸化学中的常规保护基，B是腺嘌呤、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-咪唑羧酸酰胺-1-基或5-氨基-4-咪唑羧酸酰胺-3-基，其中，如果B是腺嘌呤、胞嘧啶或鸟嘌呤，则主要氨基功能可能具有永久性保护基。这些衍生物可用于在DNA芯片上进行光控制合成寡核苷酸。
• NUCLEOSID-DERIVATE MIT PHOTOLABILEN SCHUTZGRUPPEN
  申请人：Pfleiderer, Wolfgang

  公开号：EP0901501B1

  公开（公告）日：2001-10-17
• US6153744A
  申请人：——

  公开号：US6153744A

  公开（公告）日：2000-11-28
• 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.
• New Photolabile Protecting Groups of the 2-(2-Nitrophenyl)ethoxycarbonyl- and the 2-(2-Nitrophenyl)ethylsulfonyl-Type for the Oligonucleotide Synthesis
  作者：S. Bühler、H. Giegrich、W. Pfleiderer

  DOI：10.1080/07328319908044692

  日期：1999.6