N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy(hydroxy)phosphoryl]oxyoxolan-2-yl]purin-6-yl]benzenecarboximidate | 71100-65-7

• 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: N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy(hydroxy)phosphoryl]oxyoxolan-2-yl]purin-6-yl]benzenecarboximidate
• CAS: 71100-65-7
• 化学式: C₄₁H₃₈N₆O₉P
• 分子量: 789.761
• InChiKey: GVJYCYIQUSHMRT-LIVOIKKVSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  57
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  196
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  5'-O-(4,4'-二甲氧基三苯基)-N6-苯甲酰基-2'-脱氧腺苷-3'-(2-氰乙基-N,N-二异丙基)亚磷酰胺 在 吡啶 、 四氮唑 、 氘代吡啶 、 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 0.92h， 生成 N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy(hydroxy)phosphoryl]oxyoxolan-2-yl]purin-6-yl]benzenecarboximidate
  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

• Nonoxidative chlorination of dialkyl phosphonates to dialkyl phosphorochloridites. A new approach to oligonucleotide synthesis
  作者：Takeshi Wada、Ryohei Kato、Tsujiaki Hata

  DOI：10.1021/jo00003a056

  日期：1991.2

  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.