5'-O-(4,4'-dimethoxytrityl)-5-cyanomethoxycarbonylmethyl-2'-deoxyuridine | 209163-81-5

• 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)-5-cyanomethoxycarbonylmethyl-2'-deoxyuridine
• 英文别名: cyanomethyl 2-[1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-2,4-dioxopyrimidin-5-yl]acetate
• CAS: 209163-81-5
• 化学式: C₃₄H₃₃N₃O₉
• 分子量: 627.651
• InChiKey: HQSTUNCHWMHWNE-FRXPANAUSA-N

物化性质

• 密度：
  1.320±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  46
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  157
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-5-cyanomethoxycarbonylmethyl-2'-deoxyuridine 在 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 生成
  参考文献：
  名称：

  Novel fluorescent oligoDNA probe bearing a multi-conjugated nucleoside with a fluorophore and a non-fluorescent intercalator as a quencher

  摘要：

  A set of 15mer linear oligoDNA probes bearing a modified nucleoside conjugated with a polyamine/fluorescein/anthraquinone reporting moiety were synthesized. In a single-stranded form, the fluorescence generated by the excitation of fluorescein was efficiently quenched, while marked recovery of the fluorescence was observed when the probes formed duplexes with the fully complementary strand. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.02.016
• 作为产物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-5-methoxycarbonylmethyl-2'-deoxyuridine 在 lithium hydroxide 、 potassium carbonate 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 7.0h， 生成 5'-O-(4,4'-dimethoxytrityl)-5-cyanomethoxycarbonylmethyl-2'-deoxyuridine
  参考文献：
  名称：

  Synthesis of a novel 2′-deoxyuridine derivative bearing a cyanomethoxycarbonylmethyl group at C-5 position and its use for versatile post-synthetic functionalization of oligodeoxyribonucleotides

  摘要：

  A novel 2'-deoxyuridine derivative bearing a cyanomethoxycarbonylmethyl group at the C-5 position (1) was synthesized and its use was examined as a convertible nucleoside for the versatile post-synthesis functionalization of oligodeoxyribonucleotides (ODNs). The ODNs containing 1 reacted with primary monoamines such as heptylamine, histamine, and tyramine as well as di- and polyamines under mild conditions, giving the corresponding derivatized ODNs. (C) 1998 Elsevier Science Ltd. AII rights reserved.

  DOI：

  10.1016/s0040-4039(98)00660-1

文献信息

• Synthesis and Duplex-Forming Property of Oligonucleotides Bearing a Novel Polyamine-Modified Intercalator at the Terminal or the Internal Position
  作者：Tomohisa Moriguchi、Hirokazu Sekiguchi、Makoto Tachibana、Kazuo Shinozuka

  DOI：10.1080/15257770600685982

  日期：2006.6

  Novel oligonucleotides bearing a polyamine-intercalator conjugate modified at the terminal or the internal position were reported. These modified oligonucleotides showed duplex-stabilization effect, and the thermodynamic analysis and the salt concentration dependency of the duplex stability revealed that the polyamine moiety also acted as the duplex stabilizer by neutralization of the phosphate negative charge.
• Novel fluorescent oligoDNA probe bearing a multi-conjugated nucleoside with a fluorophore and a non-fluorescent intercalator as a quencher
  作者：Sinichi Kodama、Satoko Asano、Tomohisa Moriguchi、Hiroaki Sawai、Kazuo Shinozuka

  DOI：10.1016/j.bmcl.2006.02.016

  日期：2006.5

  A set of 15mer linear oligoDNA probes bearing a modified nucleoside conjugated with a polyamine/fluorescein/anthraquinone reporting moiety were synthesized. In a single-stranded form, the fluorescence generated by the excitation of fluorescein was efficiently quenched, while marked recovery of the fluorescence was observed when the probes formed duplexes with the fully complementary strand. (C) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of a novel 2′-deoxyuridine derivative bearing a cyanomethoxycarbonylmethyl group at C-5 position and its use for versatile post-synthetic functionalization of oligodeoxyribonucleotides
  作者：Satoru Kohgo、Kazuo Shinozuka、Hiroaki Ozaki、Hiroaki Sawai

  DOI：10.1016/s0040-4039(98)00660-1

  日期：1998.6

  A novel 2'-deoxyuridine derivative bearing a cyanomethoxycarbonylmethyl group at the C-5 position (1) was synthesized and its use was examined as a convertible nucleoside for the versatile post-synthesis functionalization of oligodeoxyribonucleotides (ODNs). The ODNs containing 1 reacted with primary monoamines such as heptylamine, histamine, and tyramine as well as di- and polyamines under mild conditions, giving the corresponding derivatized ODNs. (C) 1998 Elsevier Science Ltd. AII rights reserved.