2-Cyanoethyl 5'-O-(dimethoxytrityl)thymidin-3'-yl N-(phenylacetyl)phosphoramidate | 169049-63-2

• 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: 2-Cyanoethyl 5'-O-(dimethoxytrityl)thymidin-3'-yl N-(phenylacetyl)phosphoramidate
• 英文别名: N-[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-(2-cyanoethoxy)phosphoryl]-2-phenylacetamide
• CAS: 169049-63-2
• 化学式: C₄₂H₄₃N₄O₁₀P
• 分子量: 794.798
• InChiKey: ILLNKZGYOQMQAX-DKIARUMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  57
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  175
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-Cyanoethyl 5'-O-(dimethoxytrityl)thymidin-3'-yl N-(phenylacetyl)phosphoramidate 在 hydroxide 作用下， 生成 Phenylacetyl-phosphoramidic acid mono-[(2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester
  参考文献：
  名称：

  Phosphitylation of Primary Carboxamides. Synthesis of Peptide-Oligonucleotide Conjugates with Acylphosphoramidate Linkages

  摘要：

  N-acylphosphoramidates can be obtained from the reaction of phosphitylated primary carboxamides and an alcohol in the presence of an acid catalyst such as tetrazole and subsequent oxidation. The reaction is useful for the preparation of peptide-oligonucleotide conjugates.

  DOI：

  10.1080/15257779508012481
• 作为产物：
  描述：

  2-苯乙酰胺 在 四氮唑 、 叔丁基过氧化氢 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.25h， 生成 2-Cyanoethyl 5'-O-(dimethoxytrityl)thymidin-3'-yl N-(phenylacetyl)phosphoramidate
  参考文献：
  名称：

  Peptide-Oligonucleotide Hybrids with N-Acylphosphoramidate Linkages

  摘要：

  The preparation of a peptide-oligonucleotide hybrid with an N-acylphosphoramidate linkage has been carried out by (i) phosphitylation of the C-terminal carboxamide of a protected peptide by reaction with a chloroalkoxy(dialkylamino)phosphine in the presence of a base, (ii) coupling of the resulting N-acylphosphorodiamidite onto an oligonucleotide-resin followed by oxidation, and (iii) deprotection and cleavage under basic conditions. The synthetic method takes advantage of the unprecedented reaction of primary carboxamides with electrophilic P-III species and takes place under mild conditions which are compatible with the stability of both the peptide and the oligonucleotide components.

  DOI：

  10.1021/jo00120a032

文献信息

• Phosphitylation of Primary Carboxamides. Synthesis of Peptide-Oligonucleotide Conjugates with Acylphosphoramidate Linkages
  作者：Anna Grandas、Jordi Robles、Enrique Pedroso

  DOI：10.1080/15257779508012481

  日期：1995.5.1

  N-acylphosphoramidates can be obtained from the reaction of phosphitylated primary carboxamides and an alcohol in the presence of an acid catalyst such as tetrazole and subsequent oxidation. The reaction is useful for the preparation of peptide-oligonucleotide conjugates.
• Peptide-Oligonucleotide Hybrids with N-Acylphosphoramidate Linkages
  作者：Jordi Robles、Enrique Pedroso、Anna Grandas

  DOI：10.1021/jo00120a032

  日期：1995.7

  The preparation of a peptide-oligonucleotide hybrid with an N-acylphosphoramidate linkage has been carried out by (i) phosphitylation of the C-terminal carboxamide of a protected peptide by reaction with a chloroalkoxy(dialkylamino)phosphine in the presence of a base, (ii) coupling of the resulting N-acylphosphorodiamidite onto an oligonucleotide-resin followed by oxidation, and (iii) deprotection and cleavage under basic conditions. The synthetic method takes advantage of the unprecedented reaction of primary carboxamides with electrophilic P-III species and takes place under mild conditions which are compatible with the stability of both the peptide and the oligonucleotide components.