2-cyanoethyl 5'-O-dimethoxytrityl-N³-benzoylthymidin-3'-yl N³,3'-O-dibenzoylthymidin-5'-yl phosphate | 109946-76-1

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 2-cyanoethyl 5'-O-dimethoxytrityl-N³-benzoylthymidin-3'-yl N³,3'-O-dibenzoylthymidin-5'-yl phosphate
• 英文别名: [(2R,3S,5R)-5-(3-benzoyl-5-methyl-2,4-dioxopyrimidin-1-yl)-2-[[[(2R,3S,5R)-5-(3-benzoyl-5-methyl-2,4-dioxopyrimidin-1-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-3-yl]oxy-(2-cyanoethoxy)phosphoryl]oxymethyl]oxolan-3-yl] benzoate
• CAS: 109946-76-1
• 化学式: C₆₅H₆₀N₅O₁₇P
• 分子量: 1214.19
• InChiKey: BZPPJNHWYBZIDE-ZIPGXIJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  88
• 可旋转键数：
  23
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  256
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  在 叔丁基过氧化氢 作用下， 以 吡啶 、 异辛烷 为溶剂， 反应 0.25h， 生成 2-cyanoethyl 5'-O-dimethoxytrityl-N³-benzoylthymidin-3'-yl N³,3'-O-dibenzoylthymidin-5'-yl phosphate
  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

文献信息

• The phosphorothioite method 2. Use of S-(t-butyl) β-cyanoethyl phosphorothioites of deoxyribonucleoside for the synthesis of oligodeoxyribonucleosides on polymer supports
  作者：Mitsuo Fujii、Hajime Nagai、Mitsuo Sekine、Tsujiaki Hata

  DOI：10.1016/s0040-4039(00)95947-1

  日期：——
• WADA, TAKESHI;KATO, RYOHEI;HATA, TSUJIAKI, J. ORG. CHEM., 56,(1991) N, C. 1243-1250
  作者：WADA, TAKESHI、KATO, RYOHEI、HATA, TSUJIAKI

  DOI：——

  日期：——
• FUJII, MITSUO;NAGAI, HAJIME;SEKINE, MITSUO;HATA, TSUJIAKI, 14TH SYMP. NUCL. ACIDS CHEM., TOKUSHIMA, OCT. 30TH - NOV. 1ST, 1986, OXFO+
  作者：FUJII, MITSUO、NAGAI, HAJIME、SEKINE, MITSUO、HATA, TSUJIAKI

  DOI：——

  日期：——