2,2,2-trichloroethyl 5'-O-dimethoxytrityl-N³-benzoylthymidin-3'-yl phosphonate | 130954-63-1

• 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: 2,2,2-trichloroethyl 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-(2,2,2-trichloroethoxyphosphonoyloxy)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 130954-63-1
• 化学式: C₄₀H₃₈Cl₃N₂O₁₀P
• 分子量: 844.082
• InChiKey: DMEQUYNBSMFNPF-BMPTZRATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  56
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  2,2,2-trichloroethyl 5'-O-dimethoxytrityl-N³-benzoylthymidin-3'-yl phosphonate 在 吡啶 、 氘代吡啶 、 二氯-三(2,4,6-三溴苯氧基)膦烷 作用下， 反应 0.08h， 以100%的产率得到Phosphorochloridous acid (2R,3S,5R)-5-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester 2,2,2-trichloro-ethyl ester
  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 生成 2,2,2-trichloroethyl 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：