1-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-(prop-1-yn-1-yl)pyrimidine-2,4(1H,3H)-dione | 644962-74-3

• 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: 1-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-(prop-1-yn-1-yl)pyrimidine-2,4(1H,3H)-dione
• 英文别名: 5'-O-(Dimethoxytrityl)-5-(1-propynyl)-2'-deoxyuridine；1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-5-prop-1-ynylpyrimidine-2,4-dione
• CAS: 644962-74-3
• 化学式: C₃₃H₃₂N₂O₇
• 分子量: 568.626
• InChiKey: DTVSAGUUMMWIAK-FRXPANAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-(prop-1-yn-1-yl)pyrimidine-2,4(1H,3H)-dione 在 copper(l) iodide 、 三乙胺 作用下， 以 甲醇 为溶剂， 生成 3-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-6-methyl-3H-furo[2,3-d]pyrimidin-2-one
  参考文献：
  名称：

  Pyrrolo-dC and pyrrolo-C: fluorescent analogs of cytidine and 2′-deoxycytidine for the study of oligonucleotides

  摘要：

  Pyrrolo-dC (1a, 6-methyl-3-(2-deoxy-beta-D-ribofuranosyl)-3H-pyrrolo[2,3-d]pyrimidin-2-one) and its cyanoethyl phosphoramidite 2a were synthesized. The latter was incorporated into oligodeoxyribonucleotides by standard automated synthesis techniques, where pyrrolo-dC was found to serve as a fluorescent analog of deoxycytidine. The cyanoethylphosphoramidite (2b) of pyrrolo-C (2a, 6-methyl-3-(P-D-ribofuranosyl)-3H-pyrrolo[2,3-d]pyrimidin-2-one) was also synthesized and may find use for the site-specific incorporation of a fluorescent cytidine analog into oligoribonucleotides. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.108
• 作为产物：
  描述：

  碘苷 在 吡啶 、 4-二甲氨基吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 1-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-(prop-1-yn-1-yl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  [EN] COMPOSITIONS FOR EDITING ASS1 TRANSCRIPTS AND METHODS THEREOF
  [FR] COMPOSITIONS D'ÉDITION DE PRODUITS DE TRANSCRIPTION D'ASS1 ET MÉTHODES ASSOCIÉES

  摘要：

  Among other things, the present disclosure provides oligonucleotides, compositions and methods thereof that can bring about specific editing of a target adenosine in a target RNA molecule. Such oligonucleotides, compositions and methods are useful to treat, prevent, or ameliorate ASS1 associated disorders, diseases and syndromes that can benefit from adenosine modification.

  公开号：

  WO2023220428A1

文献信息

• Synthesis and properties of DNA oligomers containing stereopure phosphorothioate linkages and C-5 modified deoxyuridine derivatives
  作者：Rintaro Iwata Hara、Reijiro Yoshino、Yohei Nukaga、Yusuke Maeda、Kazuki Sato、Takeshi Wada

  DOI：10.1039/d0ra06970a

  日期：——

  substituent of uracil in a DNA/RNA hybrid duplex, the combination of the stereochemistry of the PS linkages and the type of the C-5 modification of uracil bases is expected to affect the properties of the hybrid duplexes. Herein, DNA oligomers containing both stereopure phosphorohioate linkages and C-5 modified deoxyuridine derivatives were synthesized. The thermodynamic stability of the DNA/RNA and DNA/DNA

  硫代磷酸酯 (PS) 修饰，其中磷酸二酯键中的非桥接氧原子被硫原子取代，被广泛用于改善核酸药物的性质。每个 PS 键都可以在两个立体异构体R p 和S p 中找到。由于S p-PS 或R中有一个非桥连氧或硫原子p-PS 分别位于 DNA/RNA 杂合双链中尿嘧啶的 C-5 取代基附近，PS 键的立体化学和尿嘧啶碱基的 C-5 修饰类型的组合预计会影响混合双链体的特性。在此，合成了含有立体纯的硫代磷酸酯键和 C-5 修饰的脱氧尿苷衍生物的 DNA 寡聚体。评估了 DNA/RNA 和 DNA/DNA 双链体的热力学稳定性以及 DNA/RNA 双链体的 RNase H 活性。DNA 链中 5-丙炔基尿嘧啶和 ( R p)-PS 键的组合可以显着提高 DNA/RNA 杂合双链体的热稳定性，而不会降低其 RNase H 活性。
• Pyrrolo-dC and pyrrolo-C: fluorescent analogs of cytidine and 2′-deoxycytidine for the study of oligonucleotides
  作者：David A. Berry、Kee-Yong Jung、Dean S. Wise、Anthony D. Sercel、William H. Pearson、Hugh Mackie、John B. Randolph、Robert L. Somers

  DOI：10.1016/j.tetlet.2004.01.108

  日期：2004.3

  Pyrrolo-dC (1a, 6-methyl-3-(2-deoxy-beta-D-ribofuranosyl)-3H-pyrrolo[2,3-d]pyrimidin-2-one) and its cyanoethyl phosphoramidite 2a were synthesized. The latter was incorporated into oligodeoxyribonucleotides by standard automated synthesis techniques, where pyrrolo-dC was found to serve as a fluorescent analog of deoxycytidine. The cyanoethylphosphoramidite (2b) of pyrrolo-C (2a, 6-methyl-3-(P-D-ribofuranosyl)-3H-pyrrolo[2,3-d]pyrimidin-2-one) was also synthesized and may find use for the site-specific incorporation of a fluorescent cytidine analog into oligoribonucleotides. (C) 2004 Elsevier Ltd. All rights reserved.