[(2R,3S,5R)-3-羟基-5-(5-甲基-2,4-二氧代嘧啶-1-基)四氢呋喃-2-基]甲基[(2R,3S,5R)-2-(羟基甲基)-5-(5-甲基-2,4-二氧代嘧啶-1-基)四氢呋喃-3-基]甲基磷酸酯 | 35002-94-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 中文名称: [(2R,3S,5R)-3-羟基-5-(5-甲基-2,4-二氧代嘧啶-1-基)四氢呋喃-2-基]甲基[(2R,3S,5R)-2-(羟基甲基)-5-(5-甲基-2,4-二氧代嘧啶-1-基)四氢呋喃-3-基]甲基磷酸酯
• 英文名称: dithymidylyl-3',5'-O-methyl phosphate
• 英文别名: [(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl [(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] methyl phosphate
• CAS: 35002-94-9
• 化学式: C₂₁H₂₉N₄O₁₂P
• 分子量: 560.455
• InChiKey: LGTAFJPHILMIHG-UGHUSNSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  203
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-3-羟基-5-(5-甲基-2,4-二氧代嘧啶-1-基)四氢呋喃-2-基]甲基[(2R,3S,5R)-2-(羟基甲基)-5-(5-甲基-2,4-二氧代嘧啶-1-基)四氢呋喃-3-基]甲基磷酸酯 在 氨 作用下， 以 水 为溶剂， 反应 8.0h， 以84%的产率得到胸苷酰(3'->5')胸苷铵盐
  参考文献：
  名称：

  Synthesis of novel cationic spermine-conjugated phosphotriester oligonucleotide for improvement of cell membrane permeability

  摘要：

  A spermine-conjugated ethyl phosphotriester oligonucleotide was obtained by solid-phase synthesis based on phosphoramidite chemistry. The ethyl phosphotriester linkage was robust to exonuclease digestion and stable in fetal bovine serum. Cell membrane permeability of the spermine-conjugated ethyl phosphotriester oligonucleotide was studied by fluorescence experiments. The effective cell penetrating potency of the spermine-conjugated ethyl phosphotriester oligonucleotide was determined by confocal laser scanning microscopy and measurement of intracellular fluorescence intensity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.06.071
• 作为产物：
  描述：

  保护胸苷 在 四氮唑 、 2-过氧化丁酮 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 8.58h， 生成 [(2R,3S,5R)-3-羟基-5-(5-甲基-2,4-二氧代嘧啶-1-基)四氢呋喃-2-基]甲基[(2R,3S,5R)-2-(羟基甲基)-5-(5-甲基-2,4-二氧代嘧啶-1-基)四氢呋喃-3-基]甲基磷酸酯
  参考文献：
  名称：

  Synthesis of novel cationic spermine-conjugated phosphotriester oligonucleotide for improvement of cell membrane permeability

  摘要：

  A spermine-conjugated ethyl phosphotriester oligonucleotide was obtained by solid-phase synthesis based on phosphoramidite chemistry. The ethyl phosphotriester linkage was robust to exonuclease digestion and stable in fetal bovine serum. Cell membrane permeability of the spermine-conjugated ethyl phosphotriester oligonucleotide was studied by fluorescence experiments. The effective cell penetrating potency of the spermine-conjugated ethyl phosphotriester oligonucleotide was determined by confocal laser scanning microscopy and measurement of intracellular fluorescence intensity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.06.071

文献信息

• Synthesis of dinucleoside phosphates and their analogs by the boranophosphotriester method using azido-based protecting groups
  作者：Toshihide Kawanaka、Mamoru Shimizu、Takeshi Wada

  DOI：10.1016/j.tetlet.2007.01.064

  日期：2007.3

  backbone-modified analogs were synthesized in good yields by the boranophosphotriester method in solution. The oligodeoxyriobonucleoside boranophosphates, fully protected with 2-(azidomethyl)benzoyl groups, were converted to the various backbone-modified DNA analogs via the corresponding H-phosphonate intermediates. A new efficient protecting group for the O6-position of 2′-deoxyguanosine, 4-[(2-azidom

  通过硼三磷酸硼酸酯方法在溶液中以高收率合成了寡脱氧核糖核苷酸及其骨架修饰的类似物。用2-（叠氮基甲基）苯甲酰基充分保护的寡脱氧核糖核苷硼酸磷酸酯通过相应的H-膦酸酯中间体转化为各种骨架修饰的DNA类似物。还开发了一种新的2'-脱氧鸟苷的O 6位有效保护基，即4-[（（2-叠氮基甲基）苯甲酰氧基]苄基（AZBn）。发现通过在二恶烷–2-巯基乙醇–H 2 O中用MePPh 2处理可以快速去除AZBn组。
• Dithymidylyl-3′,5′-phosphorofluoridates: new synthesis and stability under solvolytic conditions
  作者：Konrad Misiura、Daria Pietrasiak、Wojciech J. Stec

  DOI：10.1039/c39950000613

  日期：——

  Dithymidylyl-3′,5′-phosphorofluoridates, prepared by nucleophilic substitution of methylselenyl by fluoride ion, are relatively unstable under solvolytic conditions and undergo rapid base-catalysed hydrolysis/methanolysis.

  通过氟离子对甲基硒的亲核取代制备的二硫代-3,5,2-氟磷酸酯在溶解条件下相对不稳定，会在碱催化下发生快速水解/甲醇分解。
• Transformation of Dinucleoside<i>S</i>-Aryl Phosphorothioates into the Corresponding<i>O</i>-Alkyl Phosphates by Use of Tributyltin Alkoxides
  作者：Shokichi Ohuchi、Hiroshi Ayukawa、Tsujiaki Hata

  DOI：10.1246/cl.1992.1501

  日期：1992.8

  Several alkyl dinucleoside phosphotriesters were easily obtained by use of the reaction of S-aryl dinucleoside phosphorothioates with tributyltin alkoxides. This reaction proceeds at room temperature under neutral conditions.

  通过使用S-芳基二核苷硫代磷酸酯与三丁基锡醇盐的反应，可以容易地获得几种烷基二核苷磷酸三酯。该反应在室温中性条件下进行。
• Remote<i> cis</i><i>−</i><i>syn</i>-Thymine [2 + 2] Dimers Are Not Repaired by Radical Cations Migrating in Duplex DNA
  作者：Anthony K. Dotse、Edna K. Boone、Gary B. Schuster

  DOI：10.1021/ja994028q

  日期：2000.7.26

  A series of DNA oligomers was prepared containing an anthraquinone derivative linked to a 5‘-end, a cis−syn-[2 + 2]thymine dimer and strategically located GG steps. These compounds were designed to test the claim that one-electron oxidation of the DNA leads to repair of remote thymine dimers. Irradiation of the anthraquinone leads to remote damage at the 5‘-G of GG steps that are positioned both before

  制备了一系列 DNA 寡聚物，其中包含与 5' 末端相连的蒽醌衍生物、顺式-syn-[2 + 2] 胸腺嘧啶二聚体和战略定位的 GG 步骤。这些化合物旨在测试 DNA 的单电子氧化导致远程胸腺嘧啶二聚体修复的说法。蒽醌的辐照导致位于胸腺嘧啶二聚体之前和之后的 GG 步骤的 5'-G 处的远程损伤，但没有可检测到的 (<3%) 胸腺嘧啶二聚体修复。这些发现与之前的一系列报道形成对比，其中据报道，当远程单电子氧化通过共价连接的含 Rh 金属嵌入剂的辐照引发时，胸腺嘧啶二聚体的修复比 GG 步骤的反应效率高 40 倍.
• Jankowski, Aleksander; Golankiewicz, Krzysztof, Polish Journal of Chemistry, 1982, vol. 56, # 10-12, p. 1563 - 1568
  作者：Jankowski, Aleksander、Golankiewicz, Krzysztof

  DOI：——

  日期：——