3'-O-t-Butyldimethylsilyl-5'-deoxy-5'-hydroxymethyl thymidine | 142325-11-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3'-O-t-Butyldimethylsilyl-5'-deoxy-5'-hydroxymethyl thymidine
• 英文别名: 1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-(2-hydroxyethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 142325-11-9
• 化学式: C₁₇H₃₀N₂O₅Si
• 分子量: 370.521
• InChiKey: VJCMTJUBIRUZRM-HZSPNIEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.91
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3'-O-t-Butyldimethylsilyl-5'-deoxy-5'-hydroxymethyl thymidine 在 吡啶 、 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 Diisopropyl-phosphoramidous acid (2R,3R,5R)-2-{2-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-ethyl}-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：

  Oligodeoxynucleotides with Extended 3'- and 5'-Homologous Internucleotide Linkages.

  摘要：

  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.

  DOI：

  10.3891/acta.chem.scand.51-0318
• 作为产物：
  描述：

  5′-deoxy-5′-C-methenyl-3′-O-(tert-butyldimethylsilyl)thymidine 在 sodium hydroxide 、 1,2-thioxane 、 BH₃*oxathiane 、 硼烷 作用下， 以61%的产率得到3'-O-t-Butyldimethylsilyl-5'-deoxy-5'-hydroxymethyl thymidine
  参考文献：
  名称：

  Oligodeoxynucleotides with Extended 3'- and 5'-Homologous Internucleotide Linkages.

  摘要：

  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.

  DOI：

  10.3891/acta.chem.scand.51-0318

文献信息

• Bifunctional nucleosides, oligomers thereof, and methods of making and
  申请人：Sanofi

  公开号：US05892024A1

  公开（公告）日：1999-04-06

  Disclosed are novel bifunctional nucleoside analogs and oligonucleosides of 3-4 bases (trimers and tetramers) and longer containing at least two consecutive internucleoside linkages of two carbon-one nitrogen atom or two carbon-one oxygen atom (3'-NCC-5', 3'-CNC-5', 3'-OCC-5') internucleoside linkages. The bifunctional nucleosides are useful for preparing the trimers and tetramers, which, in turn, are useful, together with the nucleosides, in preparing oligonucleosides as well as chimeric oligonucleotide analogs, preferably antisense oligonucleosides and oligonucleotide analogs, of 6 to about 60 bases having at least two consecutive internucleoside linkages of two carbon atoms and one nitrogen atom or 2 carbon atoms and one oxygen atom in the oligonucleoside backbone.

  揭示了一种新型的双功能核苷类似物和含有至少两个连续的核苷酸连接的3-4个碱基（三聚体和四聚体）及更长的寡核苷酸。这些连接是二碳-一氮原子或二碳-一氧原子（3'-NCC-5'，3'-CNC-5'，3'-OCC-5'）之间的核苷酸连接。这些双功能核苷类似物可用于制备三聚体和四聚体，这些三聚体和四聚体与核苷酸一起可用于制备寡核苷酸以及嵌合寡核苷酸类似物，最好是6至约60个碱基的具有至少两个连续的二碳原子和一个氮原子或两个碳原子和一个氧原子的核苷酸骨架的反义寡核苷酸和寡核苷酸类似物。
• Oligonucleotide analogues containing phosphate diester linkage
  申请人：Sanofi

  公开号：US05677439A1

  公开（公告）日：1997-10-14

  The present invention relates to compounds, compositions and methods for inhibiting gene expression. The compounds of this invention comprise 1) oligonucleoside sequences of from about 6 to about 200 bases having a three atom internucleoside linkage or 2) oligonucleotide sequences of from about 9 to about 200 bases having a diol at either or both termini.

  本发明涉及抑制基因表达的化合物、组成物和方法。本发明的化合物包括1）由大约6到大约200个碱基组成，具有三个原子的核苷酸序列，或2）由大约9到大约200个碱基组成，两端具有二醇基团的寡核苷酸序列。
• 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.