5'-O-(4,4'-dimethoxytrityl)-3'-C,4'-C-(3-oxabutylene)thymidine | 1146340-54-6

• 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)-3'-C,4'-C-(3-oxabutylene)thymidine
• CAS: 1146340-54-6
• 化学式: C₃₄H₃₆N₂O₈
• 分子量: 600.668
• InChiKey: KBZYPOYGTOBRCO-KINHPLIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  44.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  121.24
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-3'-C,4'-C-(3-oxabutylene)thymidine 、 双(二异丙基氨基)(2-氰基乙氧基)膦 在 4,5-二氰基咪唑 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 以42%的产率得到1-[3'-O-(N,N-diisopropylamino-β-cyanoethoxyphosphino)-5'-O-(4,4'-dimethoxytrityl)-3'-C,4'-C-(3-oxabutylene)]thymidine
  参考文献：
  名称：

  Synthesis and Properties of 2’-Deoxy-trans-3’,4’-BNA with S-Type Sugar Puckering

  摘要：

  2'-deoxy-trans-3',4'-BNA monomer, which was previous synthesized as part of a study on bridged nucleic acids with S-type sugar puckering, was introduced into an oligodeoxynucleotide using phosphoramidite chemistry, and the hybridization ability of the 2'-deoxy-trans-3',4'-BNA-modified oligonucleotide with complementary DNA and RNA strands was evaluated. The 2'-deoxy-trans-3',4'-BNA-modified oligonucleotide showed greatly improved hybridization ability compared to its 2'-methoxy congener (2'-methoxy-trans-3',4'-BNA), which suggested that the sugar-restriction of nucleic acids to S-type conformation with appropriate design may be useful for development of DNA mimics.

  DOI：

  10.3987/com-08-s(f)99
• 作为产物：
  描述：

  1-[(2R,3aS,7aS)-3a-hydroxy-7a-(hydroxymethyl)-3,4,5,7-tetrahydro-2H-furo[2,3-c]pyran-2-yl]-5-methylpyrimidine-2,4-dione 、 4,4'-dimethoxytrityl triflate 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以99 mg的产率得到5'-O-(4,4'-dimethoxytrityl)-3'-C,4'-C-(3-oxabutylene)thymidine
  参考文献：
  名称：

  Synthesis and Properties of 2’-Deoxy-trans-3’,4’-BNA with S-Type Sugar Puckering

  摘要：

  2'-deoxy-trans-3',4'-BNA monomer, which was previous synthesized as part of a study on bridged nucleic acids with S-type sugar puckering, was introduced into an oligodeoxynucleotide using phosphoramidite chemistry, and the hybridization ability of the 2'-deoxy-trans-3',4'-BNA-modified oligonucleotide with complementary DNA and RNA strands was evaluated. The 2'-deoxy-trans-3',4'-BNA-modified oligonucleotide showed greatly improved hybridization ability compared to its 2'-methoxy congener (2'-methoxy-trans-3',4'-BNA), which suggested that the sugar-restriction of nucleic acids to S-type conformation with appropriate design may be useful for development of DNA mimics.

  DOI：

  10.3987/com-08-s(f)99