1-[3'-O-(N,N-diisopropylamino-β-cyanoethoxyphosphino)-5'-O-(4,4'-dimethoxytrityl)-3'-C,4'-C-(3-oxabutylene)]thymidine | 1146340-56-8

• 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: 1-[3'-O-(N,N-diisopropylamino-β-cyanoethoxyphosphino)-5'-O-(4,4'-dimethoxytrityl)-3'-C,4'-C-(3-oxabutylene)]thymidine
• 英文别名: 3-[[(2R,3aS,7aR)-7a-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-2-(5-methyl-2,4-dioxopyrimidin-1-yl)-3,4,5,7-tetrahydro-2H-furo[2,3-c]pyran-3a-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
• CAS: 1146340-56-8
• 化学式: C₄₃H₅₃N₄O₉P
• 分子量: 800.889
• InChiKey: XRUFRBZDDVSERH-RCSKIMPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  57
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  141
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  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