5′-O-(dimethoxytrityl)-2′-O-(tert-butyldimethylsilyl)-N2-phenoxyacetylguanosine | 121058-84-2

• 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-(dimethoxytrityl)-2′-O-(tert-butyldimethylsilyl)-N2-phenoxyacetylguanosine
• 英文别名: N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-[tert-butyl(dimethyl)silyl]oxy-4-hydroxyoxolan-2-yl]-6-oxo-1H-purin-2-yl]-2-phenoxyacetamide
• CAS: 121058-84-2
• 化学式: C₄₅H₅₁N₅O₉Si
• 分子量: 834.014
• InChiKey: XPYPOARJDHWYJZ-AEGBRLROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.81
• 重原子数：
  60
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  164
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  5′-O-(dimethoxytrityl)-2′-O-(tert-butyldimethylsilyl)-N2-phenoxyacetylguanosine 在 4-二甲氨基吡啶 、 硼酸 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 N2-phenoxyacetyl-5′-O-(4,4′-dimethoxytrityl)-2′-O-t-butyldimethylsilyl-6-(2-cyanoethyl)selenoguanosine
  参考文献：
  名称：

  Synthesis of 6-Se-Guanosine RNAs for Structural Study

  摘要：

  6-Se-guanosine phosphoramidite and RNAs have been synthesized by selenium substitution of the 6-oxygen atom, and it is revealed that the Se-derivatization is relatively stable and that bulge and wobble structures can better accommodate a large Se atom than a duplex. This Se-modification is useful in the structural study of RNAs and their protein complexes.

  DOI：

  10.1021/ol401698n
• 作为产物：
  描述：

  N2-phenoxyacetyl-5'-O-(4,4'-dimethoxytrityl)guanosine 在 吡啶 、 磷酸单苯酯 、 金刚烷酰氯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 甘油 作用下， 以 吡啶 为溶剂， 反应 48.17h， 生成 5′-O-(dimethoxytrityl)-2′-O-(tert-butyldimethylsilyl)-N2-phenoxyacetylguanosine
  参考文献：
  名称：

  High yield protection of purine ribonucleosides for phosphoramidite RNA synthesis

  摘要：

  We report high yield procedures for protection of purine ribonucleosides based on a reaction which allows concomitant highly regiospecific 2'-silylation and 3'-phosphitylation. Subsequent cleavage of the H-phosphonate monoester moiety without silyl migration provides intermediates ready for phosphitylation by standard methods to give fully protected phosphoramidites. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00733-9

文献信息

• The use of labile base protecting groups in oligoribonucleotide synthesis
  作者：Carole Chaix、Didier Molko、Robert Téoule

  DOI：10.1016/s0040-4039(01)80326-9

  日期：——

  The use of phenoxyacetyl group for the protection of the exocyclic amino function of purine bases and acetyl group for cytosine in oligonucleotide synthesis by the cyanoethylphosphoramidite approach is described. A side reaction - i.e. partial replacement of phenoxyacetyl group of protected guanines by acetyl group - was observed during the capping step. It can be avoided by the use of phenoxyacetic

  描述了在通过氰基乙基亚磷酰胺方法合成寡核苷酸中，苯氧基乙酰基用于保护嘌呤碱基的环外氨基官能团和乙酰基用于胞嘧啶。在加盖步骤中观察到了副反应，即被保护的鸟嘌呤的苯氧基乙酰基部分被乙酰基部分取代。可以通过使用苯氧乙酸酐代替乙酸酐来避免这种情况。
• Automated Solid-Phase Synthesis of RNA Oligonucleotides Containing a Nonbridging Phosphorodithioate Linkage via Phosphorothioamidites
  作者：Nan-Sheng Li、John K. Frederiksen、Joseph A. Piccirilli

  DOI：10.1021/jo301834p

  日期：2012.11.2

  This work describes a general method for the synthesis of oligoribonucleotides containing a site-specific nonbridging phosphorodithioate linkage via automated solid-phase synthesis using 5′-O-DMTr-2′-O-TBS-ribonucleoside 3′-N,N-dimethyl-S-(2,4-dichlorobenzyl) phosphorothioamidites (2a–2d). The 3′-phosphorothioamidites (2a–2d) can be conveniently prepared in good yields (86–99%) via a one-pot reaction

  这项工作描述了一种通过使用 5'- O -DMTr-2'- O -TBS-核糖核苷 3'- N , N -二甲基- S -(2,4-二氯苄基)磷硫代酰胺 ( 2a – 2d )。3'- phosphorothioamidites（2A - 2D）可以以良好的产率（86-99％），通过从相应的5'-单釜反应方便地制备ö -DMTr -2'- ö -TBS核糖核苷（1A - 1d )。
• WO2008/8476
  申请人：——

  公开号：——

  公开（公告）日：——
• CHAIX, CAROLE;MOLKO, DIDIER;TEOULE, ROBERT, TETRAHEDRON LETT., 30,(1989) N 1, C. 71-74
  作者：CHAIX, CAROLE、MOLKO, DIDIER、TEOULE, ROBERT

  DOI：——

  日期：——