N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[chloro(2-cyanoethoxy)phosphanyl]oxyoxolan-2-yl]purin-6-yl]benzamide | 119484-02-5

• 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-[chloro(2-cyanoethoxy)phosphanyl]oxyoxolan-2-yl]purin-6-yl]benzamide
• CAS: 119484-02-5
• 化学式: C₄₁H₃₈ClN₆O₇P
• 分子量: 793.215
• InChiKey: PUWHHDODNQSHQA-MICLYWDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.17
• 重原子数：
  56.0
• 可旋转键数：
  16.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  151.87
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[chloro(2-cyanoethoxy)phosphanyl]oxyoxolan-2-yl]purin-6-yl]benzamide 在 水 、 碘 作用下， 以 吡啶 为溶剂， 生成 [(2R,3S,5R)-2-[[[(2R,3S,5R)-5-(6-benzamidopurin-9-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-3-yl]oxy-(2-cyanoethoxy)phosphoryl]oxymethyl]-5-(3-benzoyl-5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] benzoate
  参考文献：
  名称：

  2-氰基乙基核苷3'-膦酸酯作为寡核苷酸合成的新原料

  摘要：

  通过使用三（2，4，6,6-三溴苯氧基）二氯磷烷（BDCP）作为氯化试剂，将包括烷基核苷3'-膦酸酯在内的各种二取代膦酸酯迅速转化为相应的次氯代磷酸酯。发现该反应适用于寡核苷酸的快速和实用合成。

  DOI：

  10.1016/s0040-4039(00)80439-6
• 作为产物：
  描述：

  [(2R,3S,5R)-5-(6-benzamidopurin-9-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-3-yl] 2-cyanoethyl hydrogen phosphite 生成 N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[chloro(2-cyanoethoxy)phosphanyl]oxyoxolan-2-yl]purin-6-yl]benzamide
  参考文献：
  名称：

  WADA, TAKESHI;HOTODA, HITOSHI;SEKINE, MITSUO;HATA, TSUJIAKI, TETRAHEDRON LETT., 29,(1988) N 33, C. 4143-4146

  摘要：

  DOI：

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.