Phosphorochloridous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-[6-(2-cyano-ethoxy)-2-isobutyrylamino-purin-9-yl]-tetrahydro-furan-3-yl ester methyl ester | 130954-70-0

• 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: Phosphorochloridous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-[6-(2-cyano-ethoxy)-2-isobutyrylamino-purin-9-yl]-tetrahydro-furan-3-yl ester methyl ester
• CAS: 130954-70-0
• 化学式: C₃₉H₄₂ClN₆O₈P
• 分子量: 789.225
• InChiKey: PKNNYAXRFWVKGJ-YUAQEYQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.52
• 重原子数：
  55.0
• 可旋转键数：
  17.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  161.1
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  Phosphorochloridous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-[6-(2-cyano-ethoxy)-2-isobutyrylamino-purin-9-yl]-tetrahydro-furan-3-yl ester methyl ester 在 吡啶 、 氘代吡啶 、 水 、 碘 作用下， 以 吡啶 、 氘代吡啶 为溶剂， 反应 0.25h， 生成 [(2R,3S,5R)-5-(3-benzoyl-5-methyl-2,4-dioxopyrimidin-1-yl)-2-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-[6-(2-cyanoethoxy)-2-(2-methylpropanoylamino)purin-9-yl]oxolan-3-yl]oxy-methoxyphosphoryl]oxymethyl]oxolan-3-yl] benzoate
  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：

  methyl 5'-O-dimethoxytrityl-N²-isobutyryl-O⁶-(2-cyanoethyl)deoxyguanosin-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)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-[6-(2-cyano-ethoxy)-2-isobutyrylamino-purin-9-yl]-tetrahydro-furan-3-yl ester methyl 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