N³-pivaloyloxymethyl-3',5'-O-(tetraisopropyldisiloxan-1,3-diyl)uridine | 195247-12-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N³-pivaloyloxymethyl-3',5'-O-(tetraisopropyldisiloxan-1,3-diyl)uridine
• 英文别名: [3-[(6aR,8R,9R,9aS)-9-hydroxy-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-2,6-dioxopyrimidin-1-yl]methyl 2,2-dimethylpropanoate
• CAS: 195247-12-2
• 化学式: C₂₇H₄₈N₂O₉Si₂
• 分子量: 600.857
• InChiKey: CCLGJSOGRSEVMU-MSNJVRRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N³-pivaloyloxymethyl-3',5'-O-(tetraisopropyldisiloxan-1,3-diyl)uridine 在 咪唑 、 四丁基氟化铵 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 吡啶 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.33h， 生成 3-N-pivaloyloxymethyl-2'-O-[1-(2-fluorophenyl)-4-methoxypiperidin-4-yl]-3'-O-(9-phenylxanthen-9-yl)uridine-5'-O-(methyl N,N-diisopropylphosphoramidite)
  参考文献：
  名称：

  Solid-phase synthesis of branched RNA and branched DNA/RNA chimeras

  摘要：

  An effective method for synthesising branched oligonucleotides on solid phase in the 5' to 3' direction has been developed. Special branch-point monomers enable the synthesis of branched oligonucleotides which can have sequences of different length and base composition attached to the 2'-and 3'-hydroxyl groups of the branch point ribonucleoside. The branched oligonucleotides are assembled on commercial DNA synthesisers, the crude products are readily purified by reversed phase HPLC and the fully deprotected products are conveniently analysed by mass spectrometry. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00731-x
• 作为产物：
  描述：

  1-((6aR,8R,9R,9aR)-2,2,4,4-tetraisopropyl-9-((trimethylsilyl)oxy)tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)pyrimidine-2,4(1H,3H)-dione 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.03h， 生成 N³-pivaloyloxymethyl-3',5'-O-(tetraisopropyldisiloxan-1,3-diyl)uridine
  参考文献：
  名称：

  Solid-phase synthesis of branched RNA and branched DNA/RNA chimeras

  摘要：

  An effective method for synthesising branched oligonucleotides on solid phase in the 5' to 3' direction has been developed. Special branch-point monomers enable the synthesis of branched oligonucleotides which can have sequences of different length and base composition attached to the 2'-and 3'-hydroxyl groups of the branch point ribonucleoside. The branched oligonucleotides are assembled on commercial DNA synthesisers, the crude products are readily purified by reversed phase HPLC and the fully deprotected products are conveniently analysed by mass spectrometry. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00731-x

文献信息

• Design of 2′-phenylethynylpyrene excimer forming DNA/RNA probes for homogeneous SNP detection: The attachment manner matters
  作者：Kira Astakhova、Andrey V. Golovin、Igor A. Prokhorenko、Alexey V. Ustinov、Irina A. Stepanova、Timofei S. Zatsepin、Vladimir A. Korshun

  DOI：10.1016/j.tet.2017.04.045

  日期：2017.6

  compared to pyrene, retaining, however, pyrene's ability to form excimers. Here we report the synthesis of 2′-O-[3(and 4)-(pyren-1-ylethynyl)benzyl]-uridines and their tandem incorporation into deoxyribo- and 2′-O-Me-ribo-oligonucleotide probes. Excimer forming probes of type NN … NNXXNN … NN (X = 2′-O-[meta(or para)-(pyren-1-ylethynyl)-benzyl]uridine) containing two adjacent fluorescent nucleosides within

  与pyr相比，1-苯基乙炔基re荧光团（1-PEPy）具有长波移发射和更高的光稳定性，但是保留了to形成准分子的能力。这里，我们报告的2'-合成ö - 〔3（和4） - （芘-1-基乙炔基）苄基] -uridines及其串联掺入脱氧核糖-和2'- ö -Me-核糖-寡核苷酸探针。寡核苷酸内含有两个相邻荧光核苷的NN…NN XX NN…NN（X  = 2'- O- [间（或对）-（吡喃-1-基乙炔基）-苄基]尿苷）型准分子形成探针四种类型（meta - meta; 第-元; 元-对; para - para）。合成了两个DNA（N =脱氧核糖核苷酸）和2'- O -Me-RNA（N = 2'- O -Me-核糖核苷酸）探针，并研究了它们与互补的和错配的DNA和RNA的杂交。几种探针在杂交后显示出其准分子与单体强度比的显着响应。值得注意的是，在2'- O内具有对-间和间-对组合的探针显示出最壮
• Oligonucleotides with 2′-O-carboxymethyl group: synthesis and 2′-conjugation via amide bond formation on solid phase
  作者：Anna Kachalova、Eugeny Zubin、Dmitry Stetsenko、Michael Gait、Tatiana Oretskaya

  DOI：10.1039/b409496d

  日期：——

  method for synthesis of oligonucleotide 2'-conjugates via amide bond formation on solid phase is described. Protected oligonucleotides containing a 2'-O-carboxymethyl group were obtained by use of a novel uridine 3'phosphoramidite, where the carboxylic acid moiety was introduced as its allyl ester. This protecting group is stable to the conditions used in solid-phase oligonucleotide assembly, but easily

  描述了通过在固相上形成酰胺键来合成寡核苷酸2'-缀合物的有效方法。通过使用新型的尿苷3'亚磷酰胺获得了含有2'-O-羧甲基的受保护的寡核苷酸，其中羧酸部分作为烯丙基酯被引入。该保护基对固相寡核苷酸组装中使用的条件稳定，但易于通过Pd（0）和吗啉处理除去。然后在正常的肽偶联条件下，将2'-O-羧甲基化的寡核苷酸有效地缀合在固体支持物上，与各种胺或小肽的N-末端结合，从而以高收率得到高纯度的产物。该方法原则上非常适合于制备在2'之间包含酰胺键的肽-寡核苷酸缀合物
• Synthesis of oligo-2′-O-methylribonucleotides containing α-amino acid residues in 2′-position
  作者：E. V. Kazanova、E. M. Zubin、V. Kachalova、D. A. Stetsenko、M. J. Gait、T. S. Oretskaya

  DOI：10.1007/s11172-007-0120-2

  日期：2007.4

  Oligo-2′-O-methylribonucleotides containing residues of phenylalanine, histidine, and lysine amides were synthesized with the use of new phosphoramidites of 2′-aminoacid derivatives of uridine.

  利用尿苷2'-氨基酸衍生物的新亚磷酰胺合成了含有苯丙氨酸、组氨酸和赖氨酸酰胺残基的寡-2'-O-甲基核糖核苷酸。
• 2′-O-Propargyl oligoribonucleotides: Synthesis and hybridisation
  作者：Morten Grøtli、Mark Douglas、Ramon Eritja、Brian S. Sproat

  DOI：10.1016/s0040-4020(98)00271-3

  日期：1998.5

  functionality, thereby enabling the synthesis of protected 2′-O-propargyl-3′-O-phosphoramidites, building blocks for the assembly of 2′-O-propargyl oligoribonucleotides. The suitability of phosphoramidite chemistry for the introduction of this modified nucleoside was proven using MALDI or ES mass spectrometry of the final oligomer. The 2′-O-propargyl oligoribonucleotides showed an increase in the Tm of

  使用亚磷酰胺方法在自动化DNA合成仪上合成了包含2'- O-炔丙基核糖核苷酸的完全修饰的寡核苷酸序列。的高选择性烷基化步骤用于引入炔丙基的功能，从而能够合成受保护的2'- ö -propargyl -3'- ø -phosphoramidites，积木用于组件的2'- ö -propargyl寡核糖核苷酸。使用最终低聚物的MALDI或ES质谱法证明了亚磷酰胺化学方法对引入这种修饰的核苷的适用性。2′- O-炔丙基寡核糖核苷酸相对于相应的RNA同源双链体，具有互补RNA的双链体的Tm增加。这些类似物应被证明可用于多种反义应用。
• 2′-O-(carbamoylmethyl)oligoribonucleotides
  作者：Morten Grøtli、Barbro Beijer、Brian Sproat

  DOI：10.1016/s0040-4020(99)00126-x

  日期：1999.4

  Fully modified oligonucleotides containing 2′-O-cyanomethylribonucleotides were synthesised on automated DNA synthesisers using protected 2′-O-cyanomethylribonucleoside-3′-O-phosphoramidite building blocks. The 2′-O-cyanomethyloligoribonucleotides were post-synthetically converted into 2′-O-carbamoylmethyloligoribonucleotides during standard deprotection conditions with aqueous ammonia. The complete

  使用受保护的2' - O-氰基甲基核糖核苷-3'- O-亚磷酰胺基结构单元，在自动化DNA合成仪上合成了包含2'- O-氰基甲基核糖核苷酸的完全修饰寡核苷酸。2'- Ô -cyanomethyloligoribonucleotides进行合成后变换成2'- ö期间用氨水标准的脱保护条件-carbamoylmethyloligoribonucleotides。使用最终低聚物的离子交换HPLC和MALDI质谱法证明了完全转化。2′- O-氨基甲酰基甲基核糖核苷酸显示，相对于相应的RNA同双链体，具有互补RNA的双链体的解链温度（Tm）大大提高。因此，这些类似物应被证明可用于多种反义应用。