5'-O-(4,4'-Dimethoxytrityl)-N⁶-(9-fluorenylmethoxycarbonyl)-2'-deoxyadenosine 3'-O-<2-cyanoethyl-N,N-diisopropylphosphoramidite>

• 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: 5'-O-(4,4'-Dimethoxytrityl)-N⁶-(9-fluorenylmethoxycarbonyl)-2'-deoxyadenosine 3'-O-<2-cyanoethyl-N,N-diisopropylphosphoramidite>
• 英文别名: N-6-Fmoc-5'-O-DMT-2'-deoxyadenosine-3'-cyanoethyl phosphoramidite；5'-O-(4,4'-Dimethoxytrityl)-N⁶-(9-fluorenylmethoxycarbonyl)-2'-deoxyadenosine 3'-O-(2-cyanoethyl-N,N-diisopropylphosphoramidite)；5'-O-DMTr-N6-Fmoc-dA-phosphoramidite；9H-fluoren-9-ylmethyl N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyoxolan-2-yl]purin-6-yl]carbamate
• 化学式: C₅₅H₅₈N₇O₈P
• 分子量: 976.081
• InChiKey: FQTBOVSKGJSPKF-HYGNTALUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  71
• 可旋转键数：
  21
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  164
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  2'-脱氧腺苷 生成 5'-O-(4,4'-Dimethoxytrityl)-N⁶-(9-fluorenylmethoxycarbonyl)-2'-deoxyadenosine 3'-O-<2-cyanoethyl-N,N-diisopropylphosphoramidite>
  参考文献：
  名称：

  The 9-Fluorenylmethoxycarbonyl (Fmoc) Group and Its Use in Oligonucleotide Synthesis

  摘要：

  The introduction of the base-labile 9-fluorenylmethoxycarbonyl (Fmoc) group into the exocyclic amino function of 2'-deoxynucleosides and their dimethoxytritylation and phosphitylation is described. The resulting key intermediates were investigated in the built-up of different oligodeoxyribonucleoside phosphate and thiophosphate chains which were deprotected under mild basic conditions leading to crude oligomers of high purity.

  DOI：

  10.1080/07328319908044667

文献信息

• Synthesis of Oligonucleotides Containing Site-specific Carcinogen Adducts. Preparation of the 2-Cyanoethyl N,N-Diisopropylphosphoramidite of N-(2'-Deoxyguanosin-8-yl)-2-(acetylamino)fluorene with Fmoc as the Base-Protecting Group
  作者：Yuanzhong Zhou、Stanislav Chladek、Louis J. Romano

  DOI：10.1021/jo00082a011

  日期：1994.2

  A 9-fluorenylmethoxycarbonyl (Fmoc) group was used to protect the exocyclic amine on the modified guanine of N-(2'-deoxyguanosin-8-yl)-2-(acetylamino)fluorene (dG-C-8-AAF) so that oligonucleotides containing a site-specific AAF adduct could be prepared. Reaction of Fmoc-Cl with dG-C-8-AAF gave N-[N-2-(9-fluorenylmethoxycarbonyl)-2'-deoxyguanosin-8-yl]-2-(acetylamino)fluorene (N2-Fmoc-dG- and N-[O-6-(9-fluorenylmethoxycarbonyl)-2'-deoxyguanosin-8-yl]-2-(acetylamino)fluorene (O-6-Fmoc-dG-C-8-AAF). The 5'-OH of N-2-FmoodG-C-8-AAF was protected using 4,4'-dimethoxrytrityl chloride to yield 5/-Dh4T-N-2-Fmoc-dG-C-8-AAF which was then reacted with 2-cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite to obtain the corresponding phosphoramidite. The phosphoramidites of Fmoc-protected dA, dC and dG were also prepared similarly. The stability of Fmoc-protected C-8-AAF-modified deoxyguanosine was studied under different conditions to establish the utility of the prepared phosphoramidite in solid-phase DNA synthesis.
• The 9-Fluorenylmethoxycarbonyl (Fmoc) Group and Its Use in Oligonucleotide Synthesis
  作者：H. Schirmeister-tichy、G. G. Alvarado、W. Pfleiderer

  DOI：10.1080/07328319908044667

  日期：1999.6

  The introduction of the base-labile 9-fluorenylmethoxycarbonyl (Fmoc) group into the exocyclic amino function of 2'-deoxynucleosides and their dimethoxytritylation and phosphitylation is described. The resulting key intermediates were investigated in the built-up of different oligodeoxyribonucleoside phosphate and thiophosphate chains which were deprotected under mild basic conditions leading to crude oligomers of high purity.