3'-O-(tert-butyldimethylsilyl)thymidine 5'-O-(methyl N,N-diisopropylphosphoramidite) | 115363-47-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3'-O-(tert-butyldimethylsilyl)thymidine 5'-O-(methyl N,N-diisopropylphosphoramidite)
• 英文别名: 1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[[di(propan-2-yl)amino]-methoxyphosphanyl]oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 115363-47-8
• 化学式: C₂₃H₄₄N₃O₆PSi
• 分子量: 517.678
• InChiKey: OZWLVYXYFOOROI-LAHROCKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  34.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  95.02
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3'-O-(tert-butyldimethylsilyl)thymidine 5'-O-(methyl N,N-diisopropylphosphoramidite) 在 四氮唑 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以96%的产率得到3'-O-(tert-butyldimethylsilyl)thymidin-5'-yl methyl phosphonate
  参考文献：
  名称：

  Conformationally Locked Nucleosides. Synthesis of Oligodeoxynucleotides Containing 3′-Amino-3′-deoxy-3′-N,5′(R)-C-ethylenethymidine

  摘要：

  3'-Amino-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3'-N,5(R)-C-ethylenethymidine (6)was synthesized starting from 3'-azido-3'-deoxythymidine. Condensation of 6 with 5'-O-(H-phosphonyl)thymidine and 5'-O-(p-nitrophenoxycarbonyl)thymidine derivatives gave dinucleotide and dinucleoside derivatives, respectively, which were incorporated into oligodeoxynucleotides (ODNs). Tm data of the modified ODNs are also presented.

  DOI：

  10.1080/15257770008033851
• 作为产物：
  描述：

  氯(二异丙基氨基)甲氧基膦 、 3'-O-(叔丁基二甲基硅烷基)胸苷 在 N,N-二异丙基乙胺 作用下， 反应 0.5h， 以89.5%的产率得到3'-O-(tert-butyldimethylsilyl)thymidine 5'-O-(methyl N,N-diisopropylphosphoramidite)
  参考文献：
  名称：

  Conformationally Locked Nucleosides. Synthesis of Oligodeoxynucleotides Containing 3′-Amino-3′-deoxy-3′-N,5′(R)-C-ethylenethymidine

  摘要：

  3'-Amino-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3'-N,5(R)-C-ethylenethymidine (6)was synthesized starting from 3'-azido-3'-deoxythymidine. Condensation of 6 with 5'-O-(H-phosphonyl)thymidine and 5'-O-(p-nitrophenoxycarbonyl)thymidine derivatives gave dinucleotide and dinucleoside derivatives, respectively, which were incorporated into oligodeoxynucleotides (ODNs). Tm data of the modified ODNs are also presented.

  DOI：

  10.1080/15257770008033851

文献信息

• 3′-Amino-2′,4′-BNA: novel bridged nucleic acids having an N3′→P5′ phosphoramidate linkage
  作者：Satoshi Obika、Mayumi Onoda、Jun-ichi Andoh、Takeshi Imanishi、Koji Morita、Makoto Koizumi

  DOI：10.1039/b105640a

  日期：——

  Novel oligonucleotide analogues, containing a 3′-amino-2′,4′-BNA unit, were successfully synthesized, and they showed superior duplex and triplex forming ability as well as BNA itself, along with remarkable enzymatic stability.

  我们成功合成了含有 3â²-氨基-2â²,4â²-BNA 单元的新型寡核苷酸类似物，这些类似物与 BNA 本身一样，具有卓越的双链和三链形成能力，并且具有显著的酶稳定性。
• Synthesis and spectroscopic analysis of branched RNA fragments: messenger RNA splicing intermediates
  作者：Masad J. Damha、Kelvin K. Ogilvie

  DOI：10.1021/jo00251a010

  日期：1988.8
• DAMHA, MASAD J.;OGILVIE, KELVIN K., J. ORG. CHEM., 53,(1988) N 16, C. 3864
  作者：DAMHA, MASAD J.、OGILVIE, KELVIN K.

  DOI：——

  日期：——