prop-2-enyl N-[9-[(2R,4S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-hydroxyoxolan-2-yl]-6-prop-2-enoxypurin-2-yl]carbamate | 175354-95-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: prop-2-enyl N-[9-[(2R,4S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-hydroxyoxolan-2-yl]-6-prop-2-enoxypurin-2-yl]carbamate
• CAS: 175354-95-7
• 化学式: C₃₃H₃₉N₅O₆Si
• 分子量: 629.788
• InChiKey: RFYAQUMONUXYJO-OYUWMTPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  45
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  prop-2-enyl N-[9-[(2R,4S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-hydroxyoxolan-2-yl]-6-prop-2-enoxypurin-2-yl]carbamate 在 四氮唑 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.5h， 生成 {6-Allyloxy-9-[(2R,4S,5R)-4-{allyloxy-[1-(3,5-dimethoxy-phenyl)-2-oxo-2-phenyl-ethoxy]-phosphanyloxy}-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-9H-purin-2-yl}-carbamic acid allyl ester
  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：

  O⁶-Allyl-N²-(allyloxycarbonyl)-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine 在 吡啶 、 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 prop-2-enyl N-[9-[(2R,4S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-hydroxyoxolan-2-yl]-6-prop-2-enoxypurin-2-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

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.