Diphenyl-carbamic acid 9-{(2R,4S,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-[chloro-(2-cyano-ethoxy)-phosphanyloxy]-tetrahydro-furan-2-yl}-2-propionylamino-9H-purin-6-yl ester | 130983-91-4

• 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: Diphenyl-carbamic acid 9-{(2R,4S,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-[chloro-(2-cyano-ethoxy)-phosphanyloxy]-tetrahydro-furan-2-yl}-2-propionylamino-9H-purin-6-yl ester
• CAS: 130983-91-4
• 化学式: C₅₀H₄₇ClN₇O₉P
• 分子量: 956.391
• InChiKey: MYTFGSHGKRWRSJ-NWOZEVOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.61
• 重原子数：
  68.0
• 可旋转键数：
  19.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  181.41
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  Diphenyl-carbamic acid 9-{(2R,4S,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-[chloro-(2-cyano-ethoxy)-phosphanyloxy]-tetrahydro-furan-2-yl}-2-propionylamino-9H-purin-6-yl ester 在 水 、 碘 作用下， 以 吡啶 、 氘代吡啶 为溶剂， 反应 0.17h， 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：

  2-cyanoethyl 5'-O-dimethoxytrityl-N²-propionyl-O⁶-diphenylcarbamoyldeoxyguanosin-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Diphenyl-carbamic acid 9-{(2R,4S,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-[chloro-(2-cyano-ethoxy)-phosphanyloxy]-tetrahydro-furan-2-yl}-2-propionylamino-9H-purin-6-yl 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