5'-O-Dimethoxytrityl-3'-acetoxymethyl-3'-deoxy-thymidine | 164007-66-3

• 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: 5'-O-Dimethoxytrityl-3'-acetoxymethyl-3'-deoxy-thymidine
• 英文别名: [(2S,3R,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]methyl acetate
• CAS: 164007-66-3
• 化学式: C₃₄H₃₆N₂O₈
• 分子量: 600.668
• InChiKey: RAXAQNMMACGOSW-RYHYHUEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5'-O-Dimethoxytrityl-3'-acetoxymethyl-3'-deoxy-thymidine 在 氨 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 为溶剂， 反应 26.0h， 生成 Diisopropyl-phosphoramidous acid (2S,3R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-ylmethyl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  An Extended Phosphate Linkage: Synthesis, Hybridization and Modeling Studies of Modified Oligonucleotides

  摘要：

  Novel stretched oligonucleotides (A-D) containing a 3'-alpha-C-methylene phosphodiester bridge (5-atoms long) have been synthesized on an automated synthesizer utilizing phosphoramidite chemistry. The key building-block 1-[3 ''-O-beta-cyanoethyldiisopropylaminophosphiryl-2,3 -dideoxy-5-O-dimethoxytriphenylmethyl-3-C-(hydroxymethyl)-beta-D-erythro-pentofuranosyl]thymine (21) was prepared in a stereoselective manner from thymidine. Hybridization studies indicated a drop (1.8-3.0 degrees C/mod.) in affinity for the complementary RNA and DNA targets. Molecular modeling results indicated that the 5-atom modified backbone had a different geometry around the phosphodiester linkage compared to the natural phosphodiester linkage. The stretched backbone may not be useful for antisense or tripler constructs, however it may find applications in biochemical/enzyme studies.

  DOI：

  10.1080/07328319608002438
• 作为产物：
  描述：

  1-[5-(tert-butyldiphenylsilyl)-2,3-dideoxy-3-C-(formyl)-β-D-erythro-pentofuranosyl]thymine 在 sodium tetrahydroborate 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 为溶剂， 反应 51.5h， 生成 5'-O-Dimethoxytrityl-3'-acetoxymethyl-3'-deoxy-thymidine
  参考文献：
  名称：

  An Extended Phosphate Linkage: Synthesis, Hybridization and Modeling Studies of Modified Oligonucleotides

  摘要：

  Novel stretched oligonucleotides (A-D) containing a 3'-alpha-C-methylene phosphodiester bridge (5-atoms long) have been synthesized on an automated synthesizer utilizing phosphoramidite chemistry. The key building-block 1-[3 ''-O-beta-cyanoethyldiisopropylaminophosphiryl-2,3 -dideoxy-5-O-dimethoxytriphenylmethyl-3-C-(hydroxymethyl)-beta-D-erythro-pentofuranosyl]thymine (21) was prepared in a stereoselective manner from thymidine. Hybridization studies indicated a drop (1.8-3.0 degrees C/mod.) in affinity for the complementary RNA and DNA targets. Molecular modeling results indicated that the 5-atom modified backbone had a different geometry around the phosphodiester linkage compared to the natural phosphodiester linkage. The stretched backbone may not be useful for antisense or tripler constructs, however it may find applications in biochemical/enzyme studies.

  DOI：

  10.1080/07328319608002438

文献信息

• Synthesis of 5′-phosphonate linked thymidine deoxyoligonucleotides
  作者：Thomas Kofoed、Marvin H. Caruthers

  DOI：10.1016/0040-4039(96)01437-2

  日期：1996.9

  idine was synthesized and coupled with 3′-deoxy-3′-hydroxy-methylthymidine to yield a 3′-COP-5′ linked thymidine dinucleotide. This dimer as its 3′-phosphoramidite was used to synthesize deoxyoligonucleotides.

  合成了5'-脱氧-5'-膦基胸苷，并与3'-脱氧-3'-羟基-甲基胸苷偶联，得到3'-CO-5P-5'连接的胸苷二核苷酸。该二聚体作为其3'-亚磷酰胺被用于合成脱氧寡核苷酸。
• Oligodeoxynucleotides with Extended 3'- and 5'-Homologous Internucleotide Linkages.
  作者：T. Kofoed、P. B. Rasmussen、P. Valentin-Hansen、E. B. Pedersen、Kari Rissanen、Wenjun Shi、Stenbjörn Styring、Cecilia Tommos、Kurt Warncke、Bryan R. Wood

  DOI：10.3891/acta.chem.scand.51-0318

  日期：——

  3'-Deoxy-3'-C-(hydroxymethyl)thymidine (3'-DHMT) and 5'-deoxy-5'-C-(hydroxymethyl)thymidine (5'-DHMT) have been prepared and used for the synthesis of novel oligodeoxynucleotides containing extended internucleotide linkages. Enzymatic stability toward exonuclease III degradation was studied and hybridization properties were tested, The extended 3'-homologous DNA causes complete cessation of exonuclease III degradation while the extended 5'-homologous DNA shows only same decrease in degradation. Duplexes having extended internucleotide linkages show a minor decrease in hybridization stability. Tripler formation with 20-mer duplexes at pH 5.5 and high salt concentration gave almost no decrease in binding affinity when compared with unmodified tripler formation. UV experiments were also performed with oligodeoxynucleotides containing hairpin structures and bulged bases, Extended linkages in the oligodeoxynucleotides gave a small increase in T-m with sequences containing a loop, but no change or only a small decrease was observed when an extra thymidine nucleotide was incorporated in the complementary strand.
• US5892024A
  申请人：——

  公开号：US5892024A

  公开（公告）日：1999-04-06