3'-O-(4,4'-dimethoxytrityl)thymidine 5'-(hydrogen butanedioate) | 140839-25-4

• 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: 3'-O-(4,4'-dimethoxytrityl)thymidine 5'-(hydrogen butanedioate)
• 英文别名: 4-(((2R,3S,5R)-3-(Bis(4-methoxyphenyl)(phenyl)methoxy)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methoxy)-4-oxobutanoic acid；4-[[(2R,3S,5R)-3-[bis(4-methoxyphenyl)-phenylmethoxy]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]-4-oxobutanoic acid
• CAS: 140839-25-4
• 化学式: C₃₅H₃₆N₂O₁₀
• 分子量: 644.678
• InChiKey: FVFGIRXTPXPIMD-FRXPANAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  47
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  150
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3'-O-(4,4'-dimethoxytrityl)thymidine 5'-(hydrogen butanedioate) 、 5'-O-[(二异丙基氨基)-(2-氰基乙氧基)氧磷基]-3'-O-(4,4'-二甲氧基三苯甲基)胸苷 以88%的产率得到5'-TTT-TT-3'
  参考文献：
  名称：

  核苷酸，第 LXV 部分，2'-脱氧核糖核苷 5'-亚磷酰胺的合成：反向 (5'-3')-寡核苷酸方法的新构件

  摘要：

  The syntheses of the 3'-O-(4,4'-dimethoxytrityl)-protected 5'-phosphoramidites 25-28 and 5'-(hydrogen succinates) 29-32, which can be used as monomeric building blocks for the inverse (5'-3')-oligodeoxyribonucleotide synthesis are described (Scheme). These activated nucleosides and nucleotides were obtained by two slightly different four-step syntheses starting with the base-protected nucleosides 13-20. For the protection of the aglycon residues, the well-established 2-(4-nitrophenyl)ethyl (npe) and [2-(4-nitrophenyl)ethoxy]carbonyl (npeoc) groups were used. The assembly of the oligonucleotides required a slightly increased coupling time of 3 min in application of the common protocol (see Table 1). The use of pyridinium hydrochloride as an activator (instead of 1H-tetrazole) resulted in an extremely shorter activation time of 30 seconds. We established the efficiency of this inverse strategy by the synthesis of the oligonucleotide 3'-conjugates 33 and 34 which carry lipophilic caps derived from cholesterol and vitamin E, respectively, as well as by the formation of (3'-3')- and (5'-5')-internucleotide linkages (see Table 2).

  DOI：

  10.1002/1522-2675(20000809)83:8<2023::aid-hlca2023>3.0.co;2-p
• 作为产物：
  描述：

  5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]thymidine 在 吡啶 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 3'-O-(4,4'-dimethoxytrityl)thymidine 5'-(hydrogen butanedioate)
  参考文献：
  名称：

  An Inverse Approach in Oligodeoxyribonucleotide Synthesis

  摘要：

  We synthesized 3'-O-dimethoxytrityl-5'O-phosphoramidites and 5'-O-succinates which can be used as monomeric building blocks for the built up of oligodeoxyribonucleotides in the alternative 5'-3' direction. With this inverse strategy oligonucleotide 3'-conjugates as well as 3'-3' and 5'-5' internucleotidic linkages can be easily formed.

  DOI：

  10.1080/07328319708006249