methyl 5'-O-dimethoxytrityl-N⁶-benzoyldeoxyadenosin-3'-yl phosphonate | 130249-64-8

• 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: methyl 5'-O-dimethoxytrityl-N⁶-benzoyldeoxyadenosin-3'-yl phosphonate
• 英文别名: N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-methoxyphosphonoyloxyoxolan-2-yl]purin-6-yl]benzamide
• CAS: 130249-64-8
• 化学式: C₃₉H₃₈N₅O₈P
• 分子量: 735.733
• InChiKey: RMTFPWDMUFGFFO-LBFZIJHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  53
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  145
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 5'-O-dimethoxytrityl-N⁶-benzoyldeoxyadenosin-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)-5-(6-benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-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
• 作为产物：
  描述：

  2-cyanoethyl 5'-O-dimethoxytrityl-N⁶-benzoyldeoxyadenosin-3'-yl phosphonate 生成 methyl 5'-O-dimethoxytrityl-N⁶-benzoyldeoxyadenosin-3'-yl phosphonate
  参考文献：
  名称：

  WADA, TAKESHI;KATO, RYOHEI;HATA, TSUJIAKI, J. ORG. CHEM., 56,(1991) N, C. 1243-1250

  摘要：

  DOI：