O⁶-Allyl-N²-(allyloxycarbonyl)-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine | 150904-00-0

• 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: O⁶-Allyl-N²-(allyloxycarbonyl)-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine
• 英文别名: prop-2-enyl N-[9-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-6-prop-2-enoxypurin-2-yl]carbamate
• CAS: 150904-00-0
• 化学式: C₂₉H₄₉N₅O₆Si₂
• 分子量: 619.909
• InChiKey: WNDXFRZGVHXCEB-BHDDXSALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.83
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  O⁶-Allyl-N²-(allyloxycarbonyl)-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine 在 四(三苯基膦)钯 diethylammonium hydrogencarbonate 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine
  参考文献：
  名称：

  O-Allyl protection of guanine and thymine residues in oligodeoxyribonucleotides

  摘要：

  DOI：

  10.1021/jo00072a050
• 作为产物：
  描述：

  烯丙醇 、 2,4,6-Trimethyl-benzenesulfonic acid 2-allyloxycarbonylamino-9-[(2R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-9H-purin-6-yl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三甲胺 作用下， 以 二氯甲烷 为溶剂， 生成 O⁶-Allyl-N²-(allyloxycarbonyl)-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine
  参考文献：
  名称：

  O-Allyl protection of guanine and thymine residues in oligodeoxyribonucleotides

  摘要：

  DOI：

  10.1021/jo00072a050

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.
• O-Allyl protection of guanine and thymine residues in oligodeoxyribonucleotides
  作者：Yoshihiro Hayakawa、Masaaki Hirose、Ryoji Noyori

  DOI：10.1021/jo00072a050

  日期：1993.9