5-(methoxymethylethynyl)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)uridine | 190451-44-6

• 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: 5-(methoxymethylethynyl)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)uridine
• 英文别名: 1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-5-(3-methoxyprop-1-ynyl)pyrimidine-2,4-dione
• CAS: 190451-44-6
• 化学式: C₃₄H₃₄N₂O₈
• 分子量: 598.653
• InChiKey: HGABGRCQMNKSOU-OJDZSJEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  双(二异丙基氨基)(2-氰基乙氧基)膦 、 5-(methoxymethylethynyl)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)uridine 在 二异丙基铵盐四氮唑 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以97%的产率得到Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-[5-(3-methoxy-prop-1-ynyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  Synthesis and DNA Duplex Stabilities of Oligonucleotides Containing C-5-(3-Methoxypropynyl)-2′-deoxyuridine Residues

  摘要：

  5'-Dimethoxytrityl-5-(3-methoxypropynyl)-2'-deoxyuridine phosphoroamidite was synthesized with the use of commercial 3-methoxypropyne. Oligonucleotides (ODNs) containing 5-(3-methoxypropynyl)-2'-deoxyuridine in different positions were prepared. The stabilities of the duplexes formed by these ODNs with the complementary templates are increased in comparison with the unmodified counterparts. On average modified residue incorporated, the Tm is raised by 1 degrees C.

  DOI：

  10.1080/07328319708001343
• 作为产物：
  描述：

  碘苷 在 copper(l) iodide 、 四(三苯基膦)钯 吡啶 、 sodium hydroxide 、 三乙胺 作用下， 以 吡啶 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.0h， 生成 5-(methoxymethylethynyl)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)uridine
  参考文献：
  名称：

  Oligodeoxynucleotides incorporating structurally simple 5-alkynyl-2′-deoxyuridines fluorometrically respond to hybridization

  摘要：

  研究表明，2â²-脱氧尿苷的精选 5- 乙炔基衍生物可对杂交产生荧光反应，并在保持双链稳定性的同时选择性地与腺嘌呤碱基配对。

  DOI：

  10.1039/b705805e

文献信息

• Oligodeoxynucleotides incorporating structurally simple 5-alkynyl-2′-deoxyuridines fluorometrically respond to hybridization
  作者：Robert H. E. Hudson、Arash Ghorbani-Choghamarani

  DOI：10.1039/b705805e

  日期：——

  Selected 5-ethynyl derivatives of 2′-deoxyuridine are shown to fluorometrically respond to hybridization and selectively base-pair to adenine whilst maintaining duplex stability.

  研究表明，2â²-脱氧尿苷的精选 5- 乙炔基衍生物可对杂交产生荧光反应，并在保持双链稳定性的同时选择性地与腺嘌呤碱基配对。
• Synthesis and DNA Duplex Stabilities of Oligonucleotides Containing C-5-(3-Methoxypropynyl)-2′-deoxyuridine Residues
  作者：Vladimir V. Tolstikov、Dmitry A. Stetsenko、Victor K. Potapov、Eugene D. Sverdlov

  DOI：10.1080/07328319708001343

  日期：1997.3

  5'-Dimethoxytrityl-5-(3-methoxypropynyl)-2'-deoxyuridine phosphoroamidite was synthesized with the use of commercial 3-methoxypropyne. Oligonucleotides (ODNs) containing 5-(3-methoxypropynyl)-2'-deoxyuridine in different positions were prepared. The stabilities of the duplexes formed by these ODNs with the complementary templates are increased in comparison with the unmodified counterparts. On average modified residue incorporated, the Tm is raised by 1 degrees C.