ethyl [2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]acetate | 197784-38-6

• 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: ethyl [2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]acetate
• 英文别名: ethyl 2-(2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl-1)-acetate；ethyl 2-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]acetate
• CAS: 197784-38-6
• 化学式: C₃₀H₃₄O₇
• 分子量: 506.596
• InChiKey: YMRMUNPZRYDFFJ-OZNIXHKMSA-N

物化性质

• 沸点：
  636.9±55.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl [2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]acetate 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 1-(1-butyn-4-yl)-1,2-dideoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranose
  参考文献：
  名称：

  Triplex-forming ability of oligonucleotides containing 1-aryl-1,2,3-triazole nucleobases linked via a two atom-length spacer

  摘要：

  Phosphoramidites containing 2-propynyloxy or 1-butyn-4-yl as nucleobase precursors were synthesized and introduced into oligonucleotides using an automated DNA synthesizer. Copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition of the oligonucleotides with various azides gave the corresponding triazolylated oligonucleotides, triplex-forming ability of these synthetic oligonucleotides with double-stranded DNA targets was evaluated by UV melting experiments. It was found that nucleobases containing 2-(1-m-carbonylaminophenyl-1,2,3-triazol-4-yl)ethyl units likely interacted with A of a TA base pair in a parallel triplex DNA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.034
• 作为产物：
  描述：

  2-脱氧-D-阿拉伯吡喃糖 在 吡啶 、 sodium ethanolate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 7.0h， 生成 ethyl [2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]acetate
  参考文献：
  名称：

  C-Glycoside phosphoramidite building block for versatile functionalization of oligodeoxyribonucleotides

  摘要：

  从 "2-脱氧-D-核糖 "开始，通过六个步骤合成了一种手性非核苷磷酸酰胺结构单元 4。它以传统方式用于机器辅助寡核苷酸合成。寡核苷酸链组装完成后，硫酯键会被各种亲核剂（氢氧根离子、丙烷-1,3-二胺、胱胺素、组胺）裂解，从而产生在寡核苷酸链中间带有一个系基的寡核苷酸共轭物。

  DOI：

  10.1039/a703059b

文献信息

• Incorporation of a novel nucleobase allows stable oligonucleotide-directed triple helix formation at the target sequence containing a purine·pyrimidine interruption
  作者：Dominique Guianvarc’h、Rachid Benhida、Jean-Louis Fourrey、Rosalie Maurisse、Jian-Sheng Sun

  DOI：10.1039/b103743a

  日期：——

  Thermal denaturation experiments have established that an oligonucleotide incorporating the artificial nucleobase S, does form a stable triplex with a double stranded DNA which exhibits a pyrimidine interruption within the oligopurine sequence.

  热变性实验证明，含有人工核碱基 S 的寡核苷酸确实能与双链 DNA 形成稳定的三倍体，双链 DNA 在寡嘌呤序列中出现嘧啶中断。
• Design of artificial nucleobases for the recognition of the AT inversion by triple-helix forming oligonucleotides: A structure–stability relationship study and neighbour bases effect
  作者：Dominique Guianvarc'h、Jean-Louis Fourrey、Rosalie Maurisse、Jian-Sheng Sun、Rachid Benhida

  DOI：10.1016/s0968-0896(03)00229-3

  日期：2003.7

  We report herein on the synthesis, the incorporation into triplex forming oligonucleotides (TFO) and the recognition properties of a series of synthetic nucleosides designed for the specific recognition of an inverted A x T base pair in a pyrimidine triple helix motif. These analogues were designed on the basis of the results obtained with our previously reported compounds S and B(t), in order to define

  我们在此报告了合成，掺入三链体形成寡核苷酸（TFO）以及一系列合成核苷的识别特性，这些序列设计用于特异性识别嘧啶三链螺旋基序中的反向A x T碱基对。这些类似物是根据我们先前报道的化合物S和B（t）获得的结果设计的，目的是定义结构稳定性关系。我们还报告了在含S的TFO的情况下，侧接S的碱基的化学性质的影响，以便获得有关A x TxS三元组内识别过程的更多信息。这项研究为更有效的类似物的概念建立了指南，以识别A x T和G x C反向碱基对。
• The Ability of 1-Aryltriazole-Containing Nucleobases to Recognize a TA Base Pair in Triplex DNA
  作者：Yoshiyuki Hari、Satoshi Obika、Motoi Nakahara、Shin Ijitsu

  DOI：10.3987/com-13-s(s)33

  日期：——

  Phosphoramidites bearing propargyl and (N-propargylcarbamoyl)methyl groups at the Cl-position of deoxyribose were synthesized and introduced into oligonucleotides by using an automated DNA synthesizer. Copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition of the oligonucleotides with various aryl azides led to triplex-forming oligonucleotides (TFOs) possessing the corresponding aryltriazole-containing nucleobases. The triplex-forming ability of TFOs with double-stranded DNA (dsDNA) was evaluated through UV-melting experiments, and it was demonstrated that m-hydroxy or m-ureido derivatives in the (1-aryltriazol-4-yl)methyl nucleobases likely interacted with a TA base pair in dsDNA.
• Ethyl[2-Deoxy-5-<i>O</i>-(4,4′-dimethoxytrityl)-α- and β-D-<i>erythro</i>-Pentofuranosyl] Acetates as Versatile Intermediates in Nucleic Acid Chemistry
  作者：Jari Hovinen、Alex Azhayev、Harri Salo、Juhani Vilpo

  DOI：10.1080/07328319908044686

  日期：1999.6

  The title compounds (1a,b) were synthesized in three steps from 2-deoxy-D-ribose, and used in the preparation of oligonucleotide conjugates, branched oligonucleotides as well as homo-N-nucleosides.
• Triplex-forming ability of oligonucleotides containing 1-aryl-1,2,3-triazole nucleobases linked via a two atom-length spacer
  作者：Yoshiyuki Hari、Motoi Nakahara、Satoshi Obika

  DOI：10.1016/j.bmc.2013.05.034

  日期：2013.9

  Phosphoramidites containing 2-propynyloxy or 1-butyn-4-yl as nucleobase precursors were synthesized and introduced into oligonucleotides using an automated DNA synthesizer. Copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition of the oligonucleotides with various azides gave the corresponding triazolylated oligonucleotides, triplex-forming ability of these synthetic oligonucleotides with double-stranded DNA targets was evaluated by UV melting experiments. It was found that nucleobases containing 2-(1-m-carbonylaminophenyl-1,2,3-triazol-4-yl)ethyl units likely interacted with A of a TA base pair in a parallel triplex DNA. (C) 2013 Elsevier Ltd. All rights reserved.