3'-O-phenoxyacetylthymidine

• 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-phenoxyacetylthymidine
• 英文别名: (C4H5O)(CH2OH)(OPac)(Th)；[(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] 2-phenoxyacetate
• 化学式: C₁₈H₂₀N₂O₇
• 分子量: 376.366
• InChiKey: KLPHTSLFMXGRBX-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3'-O-phenoxyacetylthymidine 在 palladium on activated charcoal 氢气 、 二甲基亚砜 、 N,N'-二环己基碳二亚胺 作用下， 生成 Phenoxy-acetic acid (2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(3-oxo-propyl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Oligonucleotides containing a covalent conformationally restricted phosphodiester analog for high-affinity triple helix formation: the riboacetal internucleotide linkage

  摘要：

  DOI：

  10.1021/ja00074a065
• 作为产物：
  描述：

  1-{5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione 、 苯氧乙酰氯 、 甲烷磺酸 在 甲醇 、 crude product 、 二氯甲烷 、 碳酸氢钠 、 SO4 、 甲苯 、 Sodium sulfate-III 、 乙酸乙酯 、 hexanes 作用下， 以 吡啶 为溶剂， 反应 21.5h， 以to afford 1 (11.4 g, 60.6%)的产率得到3'-O-phenoxyacetylthymidine
  参考文献：
  名称：

  Nuclease stable and binding competent oligomers and methods for their use

  摘要：

  本发明揭示了具有修饰的核苷酸间连接的寡聚物，可以通过与互补的核酸序列结合形成三链和双链结构。本发明的寡聚物可以被纳入载体中，并可以构建成任何所需的序列。本发明的组合物可用于诊断目的，以便检测病毒或疾病状况。

  公开号：

  US05792608A1

文献信息

• Facile Synthesis of Oligonucleotide Phosphoroselenoates
  作者：Kha Tram、Xiaolu Wang、Hongbin Yan

  DOI：10.1021/ol702305v

  日期：2007.11.1

  Se-(2-cyanoethyl)phthalimide was synthesized from di-(2-cyanoethyl) diselenide. This reagent was found to be an efficient selenium transfer reagent in the synthesis of selenophosphates. Thus, nucleotide H-phosphonate diesters that are formed in situ through the H-phosphonate chemistry undergo quantitative reaction with Se-(2-cyanoethyl)phthalamide. The resulting Se-(2-cyanoethyl) oligonucleotide phosphoroselenoate

  由二（2-氰基乙基）二硒化物合成Se-（2-氰基乙基）邻苯二甲酰亚胺。发现该试剂是硒代磷酸酯合成中的有效硒转移试剂。因此，通过H-膦酸酯化学原位形成的核苷酸H-膦酸酯二酯与Se-（2-氰基乙基）邻苯二甲酰胺进行定量反应。随后将所得的Se-（2-氰基乙基）寡核苷酸亚油酸三酯进行脱保护，以优异的产率得到寡核苷酸亚油酸二酯。
• Nucleoside H-boranophosphonates: a new class of boron-containing nucleotide analogues
  作者：Renpei Higashida、Natsuhisa Oka、Toshihide Kawanaka、Takeshi Wada

  DOI：10.1039/b901045a

  日期：——

  A study on the synthesis of nucleosideH-boranophosphonates, a new class of nucleotide analogues having a P→BH3 and a P–H group, via condensation of the corresponding nucleosides with H-boranophosphonate derivatives is described.

  本文描述了一项关于合成核苷H-硼基磷酸酯的研究，这是一类具有P→BH3和P–H基团的新型核苷类似物，通过将相应的核苷与H-硼基磷酸酯衍生物缩合而成。
• New solid phase synthesis of oligodeoxythymidine phosphorodithioates by a modified HObt-method
  作者：Anne B. Eldrup、Jakob Felding、Jan Kehler、Otto Dahl

  DOI：10.1016/0040-4039(95)01106-r

  日期：1995.8

  Two new dithiophosphorylating reagents have been prepared and shown to give nucleoside monomers with reactivities suitable for solid phase synthesis. An octamer and a nonamer deoxythymidine phosphorodithioate were prepared on a TentaGel support with good coupling efficiencies. The products after deblocking are free from phosphorothioate contaminations (detection limit 0.5%).

  已经制备了两种新的二硫代磷酸化试剂，显示出它们可以提供具有适于固相合成的反应性的核苷单体。在TentaGel载体上以良好的偶联效率制备了八聚体和九聚体脱氧胸苷二硫代磷酸酯。解封后的产品不含硫代磷酸酯污染物（检出限为0.5％）。
• Chemical Synthesis of Oligodeoxyribonucleotides Using <i>N</i>-Unprotected <i>H</i>-Phosphonate Monomers and Carbonium and Phosphonium Condensing Reagents:  <i>O</i>-Selective Phosphonylation and Condensation
  作者：Takeshi Wada、Yuichi Sato、Fumio Honda、Shun-ichi Kawahara、Mitsuo Sekine

  DOI：10.1021/ja9726015

  日期：1997.12.1

  Oligodeoxyribonucleotides were synthesized using H-phosphonate monomers without amino protection. The H-phosphonate monomers of deoxyadenosine, deoxycytidine, and deoxyguanosine bearing the free amino groups were synthesized in good yields by O-selective phosphonylation of the parent 5'-O-(dimethoxytrityl)deoxyribonucleosides. It was found that the amino groups of the nucleosides were not modified during internucleotidic bond formation where (benzotriazol-1-yloxy)carbonium and -phosphonium compounds were employed as condensing reagents. The most effective condensing reagent for rapid internucleotidic bond formation was found to be 2-(benzotriazol-1-yloxy)-1,1-dimethyl-2-hexafluorophosphate (BOMP). In the present H-phosphonate method, 2-(phenylsulfonyl)-3-(3-nitrophenyl)oxaziridine (PNO) was employed as a new oxidizing reagent for the oxidation of internucleotidic H-phosphonate linkages under anhydrous conditions in the presence of N,O-bis(trimethylsilyl)acetamide. The reaction mechanism for the O-selective condensation was investigated in detail by means of P-31 NMR spectroscopy. Unprecedented oxidation of the H-phosphonate monomers was observed during activation of the monomers with (benzotriazol-1-yloxy)phosphonium and -carbonium condensing reagents in the absence of the 5'-hydroxyl components. A mechanism for the O-selective condensation was proposed on the basis of ab initio molecular orbital calculations for the model compounds at the HF/6-31G* level.
• Preparation of formacetal-linked purine-purine dinucleotide analogs
  作者：Gong-Xin He、Norbert Bischofberger

  DOI：10.1016/s0040-4039(97)00004-x

  日期：1997.2

  Protected formacetal-linked purine-purine dinucleotide analogs, including dG-f-dG, dG-f-dA, dA-f-dG, and dA-f-dA, were synthesized for the first time in 40 - 60% yields by condensation of the 5'-OH group with the 3'-OCH2SCH3 group of the two corresponding deoxynucleoside units using N-iodosuccinimide in the presence of 2.5 eq of trifluoromethanesulfonic acid at -30 degrees C. (C) 1997, Elsevier Science Ltd.