methyl [3'-O-(tert-butyldimethylsilyl)thymidine-5'-carboxamido]acetate | 1246949-84-7

• 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: methyl [3'-O-(tert-butyldimethylsilyl)thymidine-5'-carboxamido]acetate
• CAS: 1246949-84-7
• 化学式: C₁₉H₃₁N₃O₇Si
• 分子量: 441.557
• InChiKey: NTZWOBIRYOKDCB-GUTXKFCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.81
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  128.72
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl [3'-O-(tert-butyldimethylsilyl)thymidine-5'-carboxamido]acetate 在 水 、 potassium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以48%的产率得到[3'-O-(tert-butyldimethylsilyl)thymidine-5'-carboxamido]acetic acid
  参考文献：
  名称：

  Oligonucleotide Analogs with Peptide Internucleotide Linkages

  摘要：

  Oligonucleotide analogs containing one or a few glycine, L-, and D-alanine or L-and D-phenylalanine residues instead of phosphodiesterinternucleotide linkages were synthesized. The stability of the duplexes formed by modified oligonucleotides and their wildtype complements was studied. Oligonucleotides with D-alanine residues in internucleotide linkages form duplexes more stable than native ones (Tm +0.2 degrees C per modification), whereas other modifications destabilize the duplexes.

  DOI：

  10.1080/15257770.2010.542790
• 作为产物：
  描述：

  3'-O-(叔丁基二甲基硅烷基)胸苷 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 benzotriazol-1-yl diethyl phosphate 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 4.0h， 生成 methyl [3'-O-(tert-butyldimethylsilyl)thymidine-5'-carboxamido]acetate
  参考文献：
  名称：

  Oligonucleotides containing a peptide internucleotide linkage. A novel class of modified oligonucleotides

  摘要：

  Oligonucleotide analogues containing one or a few glycine, L-, and D-alanine residues instead of phosphodiester internucleotide linkages were synthesized (C3'-NH-C(O)-CH(X)-NH-C(O)-C4', where X = H, (S)-CH3, and (R)-CH3. The stability of the duplexes of modified oligonucleotides with their wild-type complements was studied. The incorporation of glycine and L-alanine residues into internucleotide linkages was shown to noticeably decrease the stability of modified duplexes as compared to that of native ones (Delta T (m similar to)a'2A degrees C per modification), whereas analogues containing D-alanine linkers form duplexes with increased stability (Delta T (m similar to)+2A degrees C per modification).

  DOI：

  10.1134/s1068162010040138