5'-O-(4,4'-dimethoxytrityl)-3'-O-benzoyluridine | 96041-77-9

• 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)-3'-O-benzoyluridine
• 英文别名: Bz(-3)[DMT(-5)]Ribf(b)-uracil-1-yl；[(2R,3S,4R,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(2,4-dioxopyrimidin-1-yl)-4-hydroxyoxolan-3-yl] benzoate
• CAS: 96041-77-9
• 化学式: C₃₇H₃₄N₂O₉
• 分子量: 650.685
• InChiKey: MAULNSIUWIKSSX-DWNQJFHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  48
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  双(二异丙基氨基)(2-氰基乙氧基)膦 、 5'-O-(4,4'-dimethoxytrityl)-3'-O-benzoyluridine 在 四氮唑 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以89%的产率得到5'-O-(4,4'-dimethoxytrityl)-3'-O-benzoyl-2'-O-(2-cyanoethyl-N,N-diisopropyl)uridine phosphoramidite
  参考文献：
  名称：

  A new synthetic protocol for labeled oligonucleotides, using a chemically cleavable universal linker

  摘要：

  A two-step general method for labeling of synthetic oligonucleotides is described. The protocol employs a cleavable universal linker, 5'-O-(4,4'-dimethoxytrityl)-3'-O-benzoyl-2'-O-(2-cyanoethyl-N,N-diisopropyl)-uridine phosphoramidite, to effect coupling to polymer-bound oligonucleotide chains. Sequentially, coupling with commercially available phosphoramidite reagent of an appropriate label (Biotin, HEX etc.) in an automated DNA synthesizer is carried out. The labeled oligomers, obtained after cleavage and deprotection reactions, are analyzed on RP-HPLC. A distinctive feature of this protocol is the recovery of free oligomers from their labeled analogs under mild conditions. The oligomers obtained are comparable to the corresponding standard oligonucleotides (HPLC). (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2006.01.063
• 作为产物：
  描述：

  1-{(2R,3R,4S,5R)-4-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-tetrahydro-furan-2-yl}-1H-pyrimidine-2,4-dione 在 肼 作用下， 生成 5'-O-(4,4'-dimethoxytrityl)-3'-O-benzoyluridine
  参考文献：
  名称：

  Lekschas, Joerg; Cech, Dieter; Rosenthal, Andre, Zeitschrift fur Chemie, 1984, vol. 24, # 9, p. 329 - 330

  摘要：

  DOI：

文献信息

• ROZNERS, EH. Z.;REKIS, A. X.;KUMPINSH, V. X.;BIZDENA, EH. O., BIOORGAN. XIMIYA, 16,(1990) N1, S. 1531-1536
  作者：ROZNERS, EH. Z.、REKIS, A. X.、KUMPINSH, V. X.、BIZDENA, EH. O.

  DOI：——

  日期：——
• Lekschas, Joerg; Cech, Dieter; Rosenthal, Andre, Zeitschrift fur Chemie, 1984, vol. 24, # 9, p. 329 - 330
  作者：Lekschas, Joerg、Cech, Dieter、Rosenthal, Andre

  DOI：——

  日期：——
• A new synthetic protocol for labeled oligonucleotides, using a chemically cleavable universal linker
  作者：Shweta Mahajan、S. Patnaik、P. Kumar、R.P. Gandhi、K.C. Gupta

  DOI：10.1016/j.bmc.2006.01.063

  日期：2006.6

  A two-step general method for labeling of synthetic oligonucleotides is described. The protocol employs a cleavable universal linker, 5'-O-(4,4'-dimethoxytrityl)-3'-O-benzoyl-2'-O-(2-cyanoethyl-N,N-diisopropyl)-uridine phosphoramidite, to effect coupling to polymer-bound oligonucleotide chains. Sequentially, coupling with commercially available phosphoramidite reagent of an appropriate label (Biotin, HEX etc.) in an automated DNA synthesizer is carried out. The labeled oligomers, obtained after cleavage and deprotection reactions, are analyzed on RP-HPLC. A distinctive feature of this protocol is the recovery of free oligomers from their labeled analogs under mild conditions. The oligomers obtained are comparable to the corresponding standard oligonucleotides (HPLC). (c) 2006 Published by Elsevier Ltd.