二苯甲基氧基双(三甲基甲硅烷基氧基)氯硅烷 | 309963-45-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 二苯甲基氧基双(三甲基甲硅烷基氧基)氯硅烷
• 中文别名: 二苯甲氧基双(三甲基硅氧基)氯硅烷
• 英文名称: benzhydroxy-bis(trimethylsiloxy)silyl chloride
• 英文别名: benzhydroxy-bis(trimethylsilyloxy)silyl chloride；benzhydryloxy-bis(trimethylsiloxy)silyl chloride；benzhydryloxybis(trimethylsilyloxy)silyl chloride；benzhydryloxy-bis(trimethylsilyloxy)chlorosilane；benzhydryloxybis(trimethylsiloxy)chlorosilane；BzH-Cl；benzhydryloxy-chloro-bis(trimethylsilyloxy)silane
• CAS: 309963-45-9
• 化学式: C₁₉H₂₉ClO₃Si₃
• 分子量: 425.147
• InChiKey: MXYRUZAVJVIZOX-UHFFFAOYSA-N

物化性质

• 沸点：
  397.4±52.0 °C(Predicted)
• 密度：
  1.046±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.17
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二苯甲基氧基双(三甲基甲硅烷基氧基)氯硅烷 在 咪唑 、 5-甲硫基四氮唑 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 (2R,3S,5R)-2-(((3-(benzhydryloxy)-1,1,1,5,5,5-hexamethyltrisiloxan-3-yl)oxy)methyl)-5-(6-oxo-2-((tris(4-methoxyphenyl)methyl)amino)-1,6-dihydro-9H-purin-9-yl)tetrahydrofuran-3-yl methyl diisopropylphosphoramidite
  参考文献：
  名称：

  Solid-Phase Synthesis, Thermal Denaturation Studies, Nuclease Resistance, and Cellular Uptake of (Oligodeoxyribonucleoside)methylborane Phosphine–DNA Chimeras

  摘要：

  The major hurdle associated with utilizing oligo-deoxyribonucleotides for therapeutic purposes is their poor delivery into cells coupled with high nuclease susceptibility. In an attempt to combine the nonionic nature and high nuclease stability of the P-C bond of methylphosphonates with the high membrane permeability, low toxicity, and improved gene silencing ability of borane phosphonates, we have focused our research on the relatively unexplored methylborane phosphine (Me-P-BH3) modification. This Article describes the automated solid-phase synthesis of mixed-backbone oligodeoxynu-cleotides (ODNs) consisting of methylborane phosphine and phosphate or thiophosphate linkages (16-mers). Nuclease stability assays show that methylborane phosphine ODNs are highly resistant to 5' and 3' exonucleases. When hybridized to a complementary strand, the ODN:RNA duplex was more stable than its corresponding ODN:DNA duplex. The binding affinity of ODNANA duplex increased at lower salt concentration and approached that of a native DNA:RNA duplex under conditions close to physiological saline, indicating that the Me-P-BH3 linkage is positively charged. Cellular uptake measurements indicate that these ODNs are efficiently taken up by cells even when the strand is 13% modified. Treatment of HeLa cells and WM-239A cells with fluorescently labeled ODNs shows significant cytoplasmic fluorescence when viewed under a microscope. Our results suggest that methylborane phosphine ODNs may prove very valuable as potential candidates in antisense research and RNAi.

  DOI：

  10.1021/ja201314q

文献信息

• Synthesis of a 3-methyluridine phosphoramidite to investigate the role of methylation in a ribosomal RNA hairpin
  作者：Helen M.-P Chui、May Meroueh、Stephen A Scaringe、Christine S Chow

  DOI：10.1016/s0968-0896(01)00283-8

  日期：2002.2

  The synthesis of a 5'-O-BzH-2'-O-ACE-protected-3-methyluridine phosphoramidite is reported [BzH, benzhydryloxy-bis(trimethylsilyloxy)silyl; ACE, bis(2-acetoxyethoxy)methyl]. The phosphoramidite was employed in solid-phase RNA synthesis to generate a series of RNA hairpins containing single or multiple modifications, including the common nucleoside pseudouridine. Three 19-nucleotide hairpin RNAs that

  据报道，合成了5'-O-BzH-2'-O-ACE-保护的3-甲基尿苷亚磷酰胺[BzH，苯甲酰氧基-双（三甲基甲硅烷基氧基）甲硅烷基； [BzH]。ACE，双（2-乙酰氧基乙氧基）甲基]。亚磷酰胺用于固相RNA合成，以生成一系列包含单个或多个修饰的RNA发夹，包括常见的核苷伪尿苷。生成了三个代表大肠杆菌23S核糖体RNA的1920环区域（G（1906）-C（1924））的19个核苷酸的发夹RNA。分别在1911、1915和1917位进行了修饰。通过热解，圆二色性和NMR光谱检查了这三种RNA的稳定性和结构。
• Pseudouridines in rRNA helix 69 play a role in loop stacking interactions
  作者：Jean-Paul Desaulniers、Yu-Cheng Chang、Raviprasad Aduri、Sanjaya C. Abeysirigunawardena、John SantaLucia, Jr.、Christine S. Chow

  DOI：10.1039/b812731j

  日期：——

  The 1H NMR spectra of RNAs representing E. coli23S rRNA helix 69 with [1,3-15N]pseudouridine modification at specific sites reveal unique roles for pseudouridine in stabilizing base-stacking interactions in the hairpin loop region.

  带有特定位点[1,3-15N]假尿苷修饰的E. coli 23S rRNA 69号螺旋的1H NMR光谱显示，假尿苷在发夹环区域中，在稳定碱基堆叠相互作用方面具有独特的作用。
• Synthesis of Helix 69 of <i>Escherichia </i><i>c</i><i>oli</i> 23S rRNA Containing Its Natural Modified Nucleosides, m³Ψ and Ψ
  作者：Helen M.-P. Chui、Jean-Paul Desaulniers、Stephen A. Scaringe、Christine S. Chow

  DOI：10.1021/jo026364m

  日期：2002.12.1

  standard base phosphoramidites to synthesize a 19-nucleotide RNA representing helix 69 of Escherichia coli 23S ribosomal RNA (rRNA) (residues 1906-1924), containing a single m(3)Psi at position 1915 and two Psi's at positions 1911 and 1917. Our synthesis of the fully modified helix 69 RNA demonstrates the ability to make milligram quantities of RNA that can be used for further high-resolution structure studies

  3-甲基伪氨吡啶（m（3）Psi）亚磷酰胺，5'-O- [苯甲氧基双（三甲基甲硅烷氧基）甲硅烷基] -2'-O- [双（2-乙酰氧基乙氧基）甲基] -3-甲基伪氨吡啶-3'-的合成据报道有（甲基-N，N-二异丙基）亚磷酰胺。对Psi N1进行选择性的新戊酰氧基甲基保护，然后在N3处进行甲基化，以生成天然存在的伪尿苷类似物。m（3）Psi亚磷酰胺与假尿苷（Psi）和标准碱基亚磷酰胺结合使用可合成代表大肠杆菌23S核糖体RNA（rRNA）（残基1906-1924）的螺旋69的19个核苷酸的RNA。 （3）位置1915处的Psi和位置1911和1917处的两个Psi。我们对完全修饰的螺旋69 RNA的合成证明了制造毫克量RNA的能力，可用于进一步的高分辨率结构研究。于位置1915处假尿苷N3位置的甲基的位点选择性引入导致RNA发夹相对于假尿苷的热力学稳定性略有增加；在1915位含有尿苷或3-甲基
• Synthesis of isotopically labeled puromycin derivatives for kinetic isotope effect analysis of ribosome catalyzed peptide bond formation
  作者：Kensuke Okuda、Amy C. Seila、Scott A. Strobel

  DOI：10.1016/j.tet.2004.10.023

  日期：2004.12

  The mechanism by which the ribosome catalyze peptide bond formation remains controversial. Here we describe the synthesis of dinucleotides that can be used in kinetic isotope effect experiments to assess the transition state of ribosome catalyzed peptide bond formation. These substrates are the isotopically labeled dinucleotide cytidylyl-(3′-5′)-3′-amino-3′-deoxy-3′-l-phenylalanyl-N6,N6-dimethyladenosine

  核糖体催化肽键形成的机制仍存在争议。在这里，我们描述了可用于动力学同位素效应实验中的二核苷酸的合成，以评估核糖体催化的肽键形成的过渡态。这些底物是同位素标记的二核苷酸胞嘧啶-（3'-5'）-3'-氨基-3'-脱氧-3'-1-苯丙氨酰基-N 6，N 6-二甲基腺苷（Cm 6 A N Phe-NH 2）和胞嘧啶-（3'-5'）-3'-氨基-3'-脱氧-3'-（1-2-羟基-3-苯基丙酰基）-N 6，N 6-二甲基腺苷（Cm 6 A NPhe-OH）。这些底物在肽键形成中具有活性，可用于测量核糖体催化的蛋白质合成中的动力学同位素效应。
• Extended Length Borane Phosphonate Nucleic Acid Compounds
  申请人：McCuen Heather Brummel

  公开号：US20100010069A1

  公开（公告）日：2010-01-14

  The present invention provides a novel method for solid-phase phosphoramidite based synthesis of borane phosphonate DNA. Also provided are novel phosphoramidite molecules, novel extended length borane phosphonate nucleic acid compounds, and methods of use thereof.

  本发明提供了一种新颖的固相磷酰胺酯基合成硼磷酸酯DNA的方法。还提供了新颖的磷酰胺酯分子、新颖的扩展长度的硼磷酸酯核酸化合物以及其使用方法。