methyl 5'-O-dimethoxytrityl-N³-benzoylthymidin-3'-yl phosphonate | 130954-60-8

• 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: methyl 5'-O-dimethoxytrityl-N³-benzoylthymidin-3'-yl phosphonate
• 英文别名: 3-benzoyl-1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-methoxyphosphonoyloxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 130954-60-8
• 化学式: C₃₉H₃₉N₂O₁₀P
• 分子量: 726.72
• InChiKey: JSPZFJALQVGYTA-BMPTZRATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  52
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 5'-O-dimethoxytrityl-N³-benzoylthymidin-3'-yl phosphonate 在 吡啶 、 水 、 碘 、 二氯-三(2,4,6-三溴苯氧基)膦烷 作用下， 以 吡啶 、 氘代吡啶 为溶剂， 反应 0.25h， 生成
  参考文献：
  名称：

  Nonoxidative chlorination of dialkyl phosphonates to dialkyl phosphorochloridites. A new approach to oligonucleotide synthesis

  摘要：

  Several dialkyl phosphonates and alkyl nucleoside 3'-phosphonates were transformed into the corresponding highly reactive phosphorochloridites without oxidation of phosphorus by use of tris(2,4,6-tribromophenoxy)-dichlorophosphorane (BDCP) as a chlorinating reagent. The reaction was applied to internucleotidic bond formation. 2-Cyanoethyl and methyl nucleoside 3'-phosphonates were prepared in high yields and were stable enough to be used as starting materials in oligonucleotide synthesis. Examination of dodecathymidylate synthesis on a polymer support, using 2-cyanoethyl or methyl nucleoside 3'-phosphonate as building blocks, showed that the 2-cyanoethyl nucleoside 3'-phosphonate was more effective.

  DOI：

  10.1021/jo00003a056
• 作为产物：
  描述：

  保护胸苷 、 二氯磷酸甲酯 生成 methyl 5'-O-dimethoxytrityl-N³-benzoylthymidin-3'-yl phosphonate
  参考文献：
  名称：

  WADA, TAKESHI;KATO, RYOHEI;HATA, TSUJIAKI, J. ORG. CHEM., 56,(1991) N, C. 1243-1250

  摘要：

  DOI：

文献信息

• A facile conversion of dialkyl phosphonates to dialkyl phosphorodithioates
  作者：Takeshi Wada、Tsujiaki Hata

  DOI：10.1016/s0040-4039(00)88515-9

  日期：1990.1

  Dialkyl phosphonates were converted into the corresponding. phosphorodithioates in three steps by one-pot procedure. The reaction was applied to the synthesis of nucleoside phosphorodithioate derivatives.

  将膦酸二烷基酯转化为相应的。通过一锅法分三步进行二硫代磷酸酯的合成。该反应被用于合成核苷二硫代磷酸酯衍生物。
• Nucleoside 3′-N,N-Dialkylphosphonamidates as novel nucleotide units for the solution-phase oligonucleotide synthesis
  作者：Takeshi Wada、Kazushige Ishikawa、Tsujiaki Hata

  DOI：10.1016/s0040-4020(01)86304-3

  日期：1993.3

  3′-N,N,-diisopropylphosphonamidate building blocks for oligonucleotide synthesis were prepared in high yields from appropriately protected nucleosides by use of chlorobis(N,N,-diisopropylamino)phosphine as a phosphitylating reagent. The 5′-dimethoxytrityl group of the nucleoside 3′-N,N-diisopropylphosphonamidates was removed selectively without cleavage of the P-N bond under mild acidic conditions

  通过使用氯代双（N，N，-二异丙基氨基）膦作为磷酸化试剂，由适当保护的核苷以高收率制备用于寡核苷酸合成的核苷3'-N，N，-二异丙基氨基膦酸酯结构单元。在温和的酸性条件下，可选择性除去核苷3'-N，N-N，N-二异丙基膦酰胺的5'-二甲氧基三苯甲基，而不会裂解PN键。发现核苷3'-N，N-二异丙基膦酰胺酸酯对叔丁基氢过氧化物的氧化具有抗性。尝试使用磷酸亚氨基酯结构单元向5'-和3'-方向延伸链，并合成了三胸苷酸。发现核苷3'-N，N，N-二异丙基膦酰胺可能用作溶液相寡核苷酸合成的3'-末端核苷酸单元。
• WADA, TAKESHI;HATA, TSUJIAKI, TETRAHEDRON LETT., 31,(1990) N1, C. 7461-7462
  作者：WADA, TAKESHI、HATA, TSUJIAKI

  DOI：——

  日期：——