N⁴-allyloxycarbonyl-2'-deoxy-5-methylcytidine | 158391-95-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: N⁴-allyloxycarbonyl-2'-deoxy-5-methylcytidine
• 英文别名: prop-2-enyl N-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-2-oxopyrimidin-4-yl]carbamate
• CAS: 158391-95-8
• 化学式: C₁₄H₁₉N₃O₆
• 分子量: 325.321
• InChiKey: SPINAVSKKNBLKP-HBNTYKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N⁴-allyloxycarbonyl-2'-deoxy-5-methylcytidine 在 吡啶 、 四氮唑 、 叔丁基过氧化氢 、 triethylamine tris(hydrogen fluoride) 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 异辛烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 4.5h， 生成 prop-2-enyl N-[1-[(2R,4S,5R)-4-[2-cyanoethoxy-[1-(3,5-dimethoxyphenyl)-2-oxo-2-phenylethoxy]phosphoryl]oxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-2-oxopyrimidin-4-yl]carbamate
  参考文献：
  名称：

  Inverse Phosphotriester DNA Synthesis Using Photochemically-Removable Dimethoxybenzoin Phosphate Protecting Groups

  摘要：

  A method has been developed to prepare short DNA sequences using light to deprotect a nucleoside 3'-phosphotriester, generating a phosphodiester useful for coupling with a free 5'-OH-nucleotide. The dimethoxybenzoin group is used as the photochemically-removable protecting group for the 3'-phosphate. Cyanoethyl is most effective as the second protecting group on the phosphodiester. Because the method is directed at the preparation and use of the DNA sequences while still bound to the support, allyl and allyloxycarbonyl protecting groups are used for the nitrogenous bases since, based on the work of Hayakawa and Noyori, they can be removed without cleaving the DNA from the support. Two simple trinucleotides have been prepared in solution using this method. It has been demonstrated that the photochemical deprotection conditions do not lead to the formation of cyclobutane dimers from adjacent T residues.

  DOI：

  10.1021/jo951593c
• 作为产物：
  描述：

  3,5-双-o-(t-丁基二甲基甲硅烷基)胸腺嘧啶脱氧核苷 在 吡啶 、 1H-1,2,4-三唑 、 ammonium hydroxide 、 triethylamine tris(hydrogen fluoride) 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 N⁴-allyloxycarbonyl-2'-deoxy-5-methylcytidine
  参考文献：
  名称：

  Inverse Phosphotriester DNA Synthesis Using Photochemically-Removable Dimethoxybenzoin Phosphate Protecting Groups

  摘要：

  A method has been developed to prepare short DNA sequences using light to deprotect a nucleoside 3'-phosphotriester, generating a phosphodiester useful for coupling with a free 5'-OH-nucleotide. The dimethoxybenzoin group is used as the photochemically-removable protecting group for the 3'-phosphate. Cyanoethyl is most effective as the second protecting group on the phosphodiester. Because the method is directed at the preparation and use of the DNA sequences while still bound to the support, allyl and allyloxycarbonyl protecting groups are used for the nitrogenous bases since, based on the work of Hayakawa and Noyori, they can be removed without cleaving the DNA from the support. Two simple trinucleotides have been prepared in solution using this method. It has been demonstrated that the photochemical deprotection conditions do not lead to the formation of cyclobutane dimers from adjacent T residues.

  DOI：

  10.1021/jo951593c

文献信息

• Inverse Phosphotriester DNA Synthesis Using Photochemically-Removable Dimethoxybenzoin Phosphate Protecting Groups
  作者：Michael C. Pirrung、Lara Fallon、David C. Lever、Steven W. Shuey

  DOI：10.1021/jo951593c

  日期：1996.1.1

  A method has been developed to prepare short DNA sequences using light to deprotect a nucleoside 3'-phosphotriester, generating a phosphodiester useful for coupling with a free 5'-OH-nucleotide. The dimethoxybenzoin group is used as the photochemically-removable protecting group for the 3'-phosphate. Cyanoethyl is most effective as the second protecting group on the phosphodiester. Because the method is directed at the preparation and use of the DNA sequences while still bound to the support, allyl and allyloxycarbonyl protecting groups are used for the nitrogenous bases since, based on the work of Hayakawa and Noyori, they can be removed without cleaving the DNA from the support. Two simple trinucleotides have been prepared in solution using this method. It has been demonstrated that the photochemical deprotection conditions do not lead to the formation of cyclobutane dimers from adjacent T residues.