triethylammonium 5'-O-dimethoxytritylthymidine 3'-H-phosphonate | 3868-27-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: triethylammonium 5'-O-dimethoxytritylthymidine 3'-H-phosphonate
• 英文别名: 5'-O-dimethoxytritylthymidine 3'-H-phosphonate triethylammonium salt；[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxyphosphinic acid;N,N-diethylethanamine
• CAS: 3868-27-7
• 化学式: C₆H₁₅N*C₃₁H₃₃N₂O₉P
• 分子量: 709.777
• InChiKey: YUFCDSCMPYDLEI-PVVUSECVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  50.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  141.55
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  triethylammonium 5'-O-dimethoxytritylthymidine 3'-H-phosphonate 生成 [(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] bis(trimethylsilyl) phosphite
  参考文献：
  名称：

  GAREGG, PER J.;REGBERG, TOR;STAWINSKI, JACEK;STROMBERG, ROGER, J. CHEM. SOC. PERKIN TRANS., 1,(1987) N 6, 1269-1273

  摘要：

  DOI：
• 作为产物：
  描述：

  bis(1,1,1,3,3,3-hexafluoropropan-2-yl) hydrogen phosphite 、 保护胸苷 生成 triethylammonium 5'-O-dimethoxytritylthymidine 3'-H-phosphonate
  参考文献：
  名称：

  TAKAKU, HIROSHI;YAMAKAGE, SHUNITCHY;SAKATSUME, OSAMU;OHTSUKI, MICHIYA, CHEM. LETT.,(1988) N 10, C. 1675-1678

  摘要：

  DOI：

文献信息

• Studies on aryl H-phosphonates. I. An efficient method for the preparation of deoxyribo- and ribonucleoside 3′-H-phosphonate monoesters by transesterification of diphenyl H-phosphonate
  作者：Jadwiga Jankowska、Michał Sobkowski、Jacek Stawiński、Adam Kraszewski

  DOI：10.1016/s0040-4039(00)76906-1

  日期：1994.5

  A convenient method for the preparation of deoxyribonucleoside and ribonucleoside 3′-H-phosphonate monoesters via transesterification of diphenyl H-phosphonate with suitable protected nucleosides in pyridine is described.

  描述了通过将二苯基H-膦酸酯与合适的受保护的核苷在吡啶中进行酯交换反应来制备脱氧核糖核苷和核糖核苷3'-H-膦酸酯单酯的简便方法。
• Acridine-Labeled Primers as Tools for the Study of Nonenzymatic RNA Oligomerization
  作者：Markus Kurz、Karin Göbel、Christian Hartel、Michael W. Göbel

  DOI：10.1002/hlca.19980810528

  日期：——

  Short, dye-labeled oligonucleotides have been used as primers in template-controlled polymerization reactions of RNA. The synthesis of appropriate acridine derivatives and their attachments to nucleic acids is described. In the nonenzymatic oligomerization of 2-methyl-1H-imidazole-activated guanosine 5′-monophosphate, two observations deserve special notice: (1) reaction rates are almost unchanged

  短的，染料标记的寡核苷酸已用作RNA的模板控制聚合反应中的引物。描述了合适的a啶衍生物的合成及其与核酸的连接。在2-甲基-1 H-咪唑活化的鸟苷5'-单磷酸的非酶促低聚反应中，有两个发现值得特别注意：（1）反应速度几乎不受Na +浓度变化的影响；（2）引物-模板双链体的构象类型（A对B）对RNA寡聚化的速率和产率具有相当大的影响。在1M Na +或K +存在下研究胞苷的掺入，该过程几乎被oligo-dG模板的四链体形成所抑制。但是，如果省略这些阳离子，则使用高达100μM的模板浓度可以观察到有效的引物延伸。RNA的非酶促自我复制的机会因此可能比以前设想的要好得多。
• Use of ammonium aryl H-phosphonates in the preparation of nucleoside H-phosphonate building blocks
  作者：Vita Ozola、Colin B Reese、Quanlai Song

  DOI：10.1016/0040-4039(96)01993-4

  日期：1996.11

  Ammonium 4-methylphenyl H-phosphonate 4c was used in the conversion of 5′-O-(dimethoxytrityl)-2′-deoxynucleoside derivatives 6 into the corresponding 3′-H-phosphonates 2, which were isolated in a high state of purity and in high yield.

  使用4-甲基苯基H-膦酸铵4c将5'- O-（二甲氧基三苯甲基）-2'-脱氧核苷衍生物6转化为相应的3'- H-膦酸酯2，并以高纯度分离得到。高产。
• Synthesis and Stability of Nucleoside 3′,5′-Cyclic Phosphate Triesters Masked with Enzymatically and Thermally Labile Phosphate Protecting Groups
  作者：Vyankat A. Sontakke、Vaishali S. Shinde、Harri Lönnberg、Mikko Ora

  DOI：10.1002/ejoc.201403227

  日期：2015.1

  Appropriately protected structurally modified nucleoside 3′,5′-cyclic monophosphates are known to show antiviral activity. For this reason, a straightforward synthesis of nucleoside 3′,5′-cyclic phosphates protected with three different enzymatically removable groups, viz. 3-acetyloxy-2,2-bis(ethoxycarbonyl)propyl (in 1 and 4), 4-acetylthio-2,2-dimethyl-3-oxobutyl (in 2), and 4-(tert-butyldisulfanyl)-2

  已知经过适当保护的结构修饰核苷 3',5'-环状单磷酸酯具有抗病毒活性。出于这个原因，核苷 3',5'-环状磷酸酯的直接合成被三个不同的酶促可去除基团保护，即。3-乙酰氧基-2,2-双（乙氧基羰基）丙基（在 1 和 4 中）、4-乙酰硫基-2,2-二甲基-3-氧丁基（在 2 中）和 4-（叔丁基二硫烷基）-2,2描述了-二甲基-3-氧代丁基（3 个）基团。通过反相 HPLC 监测在 pH 7.5 和 37°C 下这些保护基团的去除情况。
• 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。