5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-(trifluoroacetamido)uridine | 118849-17-5

• 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: 5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-(trifluoroacetamido)uridine
• 英文别名: 5'-O-(4,4'-dimethoxytrityl)-2'-(trifluoroacetylamido)-2'-deoxyuridine；5'-O-(4,4'-dimethoxytrityl)-2'-trifluoroacetamido-2'-deoxyuridine；5'-O-(4,4'-dimethoxytrityl)-2'-N-trifluoroacetyl-2'-deoxyuridine；TfaNH(-2d)[DMT(-5)]Ribf(b)-uracil-1-yl；N-[(2R,3R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxyoxolan-3-yl]-2,2,2-trifluoroacetamide
• CAS: 118849-17-5
• 化学式: C₃₂H₃₀F₃N₃O₈
• 分子量: 641.601
• InChiKey: YXCGJVZWZXPKKD-YULOIDQLSA-N

物化性质

• 密度：
  1.45±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  46
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  136
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-(trifluoroacetamido)uridine 在 ammonium hydroxide 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 12.0h， 生成 N⁴-benzoyl-3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-2'-trifluoroacetamido-2'-deoxycytidine
  参考文献：
  名称：

  2‘-Amino-2‘-deoxyuridine via an Intramolecular Cyclization of a Trichloroacetimidate

  摘要：

  DOI：

  10.1021/jo9510548
• 作为产物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-2'-N,3'-O-(2-(trichloromethyl)oxazolino)-2'-deoxy-1-(β-D-ribofuranosyl)uracil 在 sodium hydroxide 、 三乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 32.0h， 生成 5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-(trifluoroacetamido)uridine
  参考文献：
  名称：

  2‘-Amino-2‘-deoxyuridine via an Intramolecular Cyclization of a Trichloroacetimidate

  摘要：

  DOI：

  10.1021/jo9510548

文献信息

• Monomers for Oligonucleotide Synthesis with Linkers Carrying Reactive Residues: II. The Synthesis of Phosphoamidites on the Basis of Uridine and Cytosine and Containing a Linker with Methoxyoxalamide Groups in Position 2′
  作者：S. V. Vasil'eva、T. V. Abramova、T. M. Ivanova、G. V. Shishkin、V. N. Sil'nikov

  DOI：10.1023/b:rubi.0000030130.99454.ae

  日期：2004.5

  A convenient preparative synthesis of 2′-amino-2′-deoxyuridine was developed. Starting from 2′-amino-2′-deoxyuridine and 2′-amino-2′-deoxycytidine, monomers for the phosphoamidite oligonucleotide synthesis were obtained that carry a linker with methoxyoxalamide groups in position 2′.

  开发了一种方便的 2'-氨基-2'-脱氧尿苷的制备合成方法。从 2'-氨基-2'-脱氧尿苷和 2'-氨基-2'-脱氧胞苷开始，获得了在 2' 位带有带有甲氧基草酰胺基团的接头的亚磷酰胺寡核苷酸合成单体。
• Synthesis and Properties of Diuridine Phosphate Analogues Containing Thio and Amino Modifications
  作者：James B. Thomson、Bhisma K. Patel、Victor Jiménez、Klaus Eckart、Fritz Eckstein

  DOI：10.1021/jo960795l

  日期：1996.1.1

  pH 9, indicating that attack on the phosphorus by the 2'-oxo anion is rate-limiting in the hydrolysis mechanism. In contrast, the rate of uridylyl (3'-5') 5'-amino-5'-deoxyuridine (UpnU) hydrolysis fell from a value of 1802 x 10(-)(6) s(-)(1) at pH 5 to 140 x 10(-)(6) s(-)(1) at pH 7.5, where it remained constant up to pH 11.5, thus indicating an acid-catalyzed reaction. The analogue 2'-amino-2'-deoxyuridylyl

  为了研究为什么用2'-氨基取代2'-羟基会阻止水解，合成了磷酸二尿苷（UpU）的几种类似物。设计这些类似物以研究2'-取代基和5'-离去基团对水解速率的影响。所有类似物都比UpU对酸碱催化的水解更加不稳定。在6到9的pH范围内，尿嘧啶（3'-5'）5'-硫代5'-脱氧尿苷（UpsU）的水解速率以对数线性方式从5 x 10的值上升。 （-）（6）s（-）（1）在pH 6到3200 x 10（-）（6）s（-）（1）在pH 9时，表明2'-氧代阴离子对磷的攻击在水解机理中是限速的。相反，尿酸（3'-5'）5'-氨基-5'的比率 -脱氧尿苷（UpnU）水解从pH 5的1802 x 10（-）（6）s（-）（1）降至pH 7.5的140 x 10（-）（6）s（-）（1） ，在高达11.5的pH值下保持恒定，因此表明是酸催化的反应。与amUpT的水解稳定性相反，类似物2'-氨基-2'-脱氧尿苷（3
• Phosphodiester Cleavage of Guanylyl-(3‘,3‘)-(2‘-amino-2‘-deoxyuridine):  Rate Acceleration by the 2‘-Amino Function
  作者：Mikko Ora、Heidi Linjalahti、Harri Lönnberg

  DOI：10.1021/ja045060+

  日期：2005.2.1

  structural analogue of guanylyl-(3‘,3‘)-uridine, guanylyl-(3‘,3‘)-(2‘-amino-2‘-deoxyuridine), having one of the 2‘-hydroxyl groups replaced with an amino function, have been followed by RP HPLC in the pH range 0−13 at 90 °C. The results are compared to those obtained earlier with guanylyl-(3‘,3‘)-uridine, guanylyl-(3‘,3‘)-(2‘,5‘-di-O-methyluridine), and uridylyl-(3‘,5‘)-uridine. Under basic conditions

  具有 2'-羟基之一的鸟苷酰-(3',3')-尿苷、鸟苷酰-(3',3')-(2'-氨基-2'-脱氧尿苷)的结构类似物的水解反应被氨基官能团取代，随后在 90 °C 下在 0-13 的 pH 范围内进行 RP HPLC。结果与之前用鸟苷酰-(3',3')-尿苷、鸟苷酰-(3',3')-(2',5'-二-O-甲基尿苷)和尿苷酰-(3 ',5')-尿苷。在碱性条件下（pH > 8），氢氧根离子催化的 P-O3' 键断裂（[OH-] 中的一级）产生 2'-氨基-2'-脱氧尿苷和鸟苷 2' 的混合物， 3'-环磷酸酯水解为鸟苷2'-和3'-磷酸酯。在这些条件下，鸟苷酰-(3',3')-(2'-氨基-2'-脱氧尿苷)的反应性比鸟苷酰-(3',3')-尿苷低10倍。在酸性和中性条件下（pH 3-8），其中裂解的 pH 速率分布由两个 pH 独立区域（从 pH 3 到 pH 4 和从 6 到 8）、鸟苷酸-(3'
• Improved synthesis of 2′-amino-2′-deoxyguanosine and its phosphoramidite
  作者：Qing Dai、Shirshendu K. Deb、James L. Hougland、Joseph A. Piccirilli

  DOI：10.1016/j.bmc.2005.08.050

  日期：2006.2

  2'-Amino-2'-deoxynucleosides and oligonucleotides containing them have proven highly effective for an array of biochemical applications. The guanosine analogue and its phosphoramidite derivatives have been accessed previously from 2'-amino-2'-deoxyuridine by transglycosylation, but with limited overall efficiency and convenience. Using simple modifications of known reaction types, we have developed

  2'-氨基-2'-脱氧核苷和包含它们的寡核苷酸已被证明对一系列生化应用非常有效。鸟苷类似物及其亚磷酰胺衍生物先前已经通过转糖基化从2'-氨基-2'-脱氧尿苷中获得，但是总体效率和便利性有限。使用已知反应类型的简单修饰，我们已经开发了有用的方案，与以前报道的相比，具有更大的便利性，更少的步骤和更高的产率来获得2'-氨基-2'-脱氧鸟苷及其两个亚磷酰胺衍生物。这些亚磷酰胺为将2'-氨基-2'-脱氧鸟苷掺入寡核苷酸中提供了有效的合成子。
• Design and synthesis of dinucleotide 5′-triphosphates with expanded functionality
  作者：Tatiana V. Abramova、Svetlana V. Vasileva、Ludmila S. Koroleva、Nina S. Kasatkina、Vladimir N. Silnikov

  DOI：10.1016/j.bmc.2008.09.029

  日期：2008.10

  We propose the new approach to the synthesis of 5 '-triphosphate derivatives of natural and modified dinucleotides with expanded functionality. Our strategy includes the combination of the solution phase synthesis of necessary dimers using the wide range of nucleic acids chemistry methods and the subsequent introduction of the triphosphate residue. A number of the new potential substrates for the template dependent synthesis of nucleic acids with expanded functionality are obtained, namely, 5 '-triphosphates of dinucleotides containing the functionally active groups in heterocyclic bases, in carbohydrate -phosphate backbone, and the groups mimicking the residues of natural amino acids. The abilities of the proposed synthetic route are also demonstrated by the synthesis of 5 '-triphosphates of dinucleotides with modified carbohydrate-phosphate backbone. (C) 2008 Elsevier Ltd. All rights reserved.