5'-O-(tert-butyldiphenylsilyl)-3'-deoxy-3'-C-(acetoxymethyl)-thymidine | 166955-34-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5'-O-(tert-butyldiphenylsilyl)-3'-deoxy-3'-C-(acetoxymethyl)-thymidine
• 英文别名: [(2S,3R,5R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]methyl acetate
• CAS: 166955-34-6
• 化学式: C₂₉H₃₆N₂O₆Si
• 分子量: 536.7
• InChiKey: LXUCQOJYILMQJG-DNRSQYFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5'-O-(tert-butyldiphenylsilyl)-3'-deoxy-3'-C-(acetoxymethyl)-thymidine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以80%的产率得到3'-Deoxy-3'-C-(acetoxymethyl)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
• 作为产物：
  描述：

  1-[5-(tert-butyldiphenylsilyl)-2,3-dideoxy-3-C-(formyl)-β-D-erythro-pentofuranosyl]thymine 在 sodium tetrahydroborate 作用下， 以 吡啶 、 乙醇 为溶剂， 反应 26.0h， 生成 5'-O-(tert-butyldiphenylsilyl)-3'-deoxy-3'-C-(acetoxymethyl)-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

• Heteroatomic oligonucleoside linkages
  申请人：Isis Pharmaceuticals, Inc.

  公开号：US06087482A1

  公开（公告）日：2000-07-11

  Oligonucleotide-mimicking macromolecules that have improved nuclease resistance are provided. Replacement of the normal phosphorodiester inter-sugar linkages found in natural oligonucleotides with four atom linking groups provide unique compounds that are useful in regulating RNA expression and in therapeutics. Methods of synthesis and use also are disclosed.

  提供了具有改善核酸酶抵抗力的寡核苷酸模拟大分子。用四原子连接基替换天然寡核苷酸中的正常磷酸二酯间糖连接，提供了独特的化合物，可用于调节RNA表达和治疗。还公开了合成和使用的方法。