3,5-bis(tert-butyldimethylsilyloxymethyl)phenylboronic acid | 1180533-48-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-bis(tert-butyldimethylsilyloxymethyl)phenylboronic acid
• 英文别名: 3,5-Bis((tert-butyldimethylsilyloxy)methyl)phenylboronic acid；[3,5-bis[[tert-butyl(dimethyl)silyl]oxymethyl]phenyl]boronic acid
• CAS: 1180533-48-5
• 化学式: C₂₀H₃₉BO₄Si₂
• 分子量: 410.509
• InChiKey: SICZIUQWNMOZRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-bis(tert-butyldimethylsilyloxymethyl)phenylboronic acid 、 胞嘧啶 在 四甲基乙二胺 、 氧气 、 copper(II) acetate monohydrate 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以91%的产率得到1-[3,5-bis(tert-butyldimethylsilyloxymethyl)phenyl]cytosine
  参考文献：
  名称：

  Synthesis and properties of a novel molecular beacon containing a benzene-phosphate backbone at its stem moiety

  摘要：

  本文描述了一种新型分子信标（MB）的合成及其性能，该分子信标的茎部分含有苯基磷酸骨架。研究发现，随着苯基磷酸骨架的引入，MB的荧光强度得到了稳定。此外，含有苯基磷酸骨架的MB对DNase I（内切酶）的抗性强于由天然DNA和2′-O-甲基-RNA组成的MB。这些结果表明，含有苯基磷酸骨架的MB相较于由天然DNA和2′-O-甲基-RNA组成的MB更具优势。

  DOI：

  10.1039/b901631g
• 作为产物：
  描述：

  在 盐酸 、 水 作用下， 以 乙醚 、 正己烷 、 乙酸乙酯 为溶剂， 以0.69 g的产率得到3,5-bis(tert-butyldimethylsilyloxymethyl)phenylboronic acid
  参考文献：
  名称：

  Synthesis and properties of a novel molecular beacon containing a benzene-phosphate backbone at its stem moiety

  摘要：

  本文描述了一种新型分子信标（MB）的合成及其性能，该分子信标的茎部分含有苯基磷酸骨架。研究发现，随着苯基磷酸骨架的引入，MB的荧光强度得到了稳定。此外，含有苯基磷酸骨架的MB对DNase I（内切酶）的抗性强于由天然DNA和2′-O-甲基-RNA组成的MB。这些结果表明，含有苯基磷酸骨架的MB相较于由天然DNA和2′-O-甲基-RNA组成的MB更具优势。

  DOI：

  10.1039/b901631g

文献信息

• Synthesis and Properties of Oligonucleotides Containing Novel Fluorescent Biaryl Units
  作者：Yoshihito Ueno、Shinji Komatsuzaki、Keiji Takasu、Satoru Kawai、Yoshiaki Kitamura、Yukio Kitade

  DOI：10.1002/ejoc.200900567

  日期：2009.10

  describe the synthesis and properties of oligonucleotides (ONs) containing biaryl units, which are composed of a bis(hydroxymethyl)benzene residue and a naphthalene or pyrene moiety. We found that by introducing the biaryl units into the ONs, the aromatic chromophores were suitably arrayed in the DNAs. Further, we succeeded in the detection of a single-base mismatch in RNA by using the ON containing the biaryl

  我们描述了含有联芳基单元的寡核苷酸 (ON) 的合成和特性，这些单元由双（羟甲基）苯残基和萘或芘部分组成。我们发现通过将联芳基单元引入 ONs，芳香族发色团在 DNA 中被适当地排列。此外，我们通过使用含有联芳基单元的 ON 作为分子信标，成功地检测了 RNA 中的单碱基错配。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• OLIGONUCLEOTIDE DERIVATIVE, LABELING AGENT AND USE FOR LABELING AGENT
  申请人：Ueno Yoshihito

  公开号：US20120126175A1

  公开（公告）日：2012-05-24

  The disclosures of the Specification provide an oligonucleotide derivative suited to practical use, as well as a fluorescent dye cluster and use therefor. The disclosures of the Specification use a labeling agent comprising a plurality of nucleotide derivative units represented by Formula (1) below: (where, Z represents a nitrogen atom or CH, Y represents an uncondensed aromatic hydrocarbon group or condensed polycyclic hydrocarbon group, X 1 represents O, S or Se, and X 2 represents SH (or S − ), S or Se − , a C I-4 alkyl or a morpholino group.)

  本规范的披露提供了适用于实际使用的寡核苷酸衍生物，以及荧光染料簇及其使用。本规范的披露使用包含由下式（1）表示的多个核苷酸衍生物单元的标记剂：（其中，Z表示氮原子或CH，Y表示未缩合的芳香族碳氢基团或缩合的多环碳氢基团，X1表示O，S或Se，X2表示SH（或S−），S或Se−，CI-4烷基或morpholino基团。）
• Oligonucleotide derivative, labeling agent and use for labeling agent
  申请人：Ueno Yoshihito

  公开号：US08354515B2

  公开（公告）日：2013-01-15

  A labeling agent comprising a plurality of nucleotide derivative units represented by Formula (1) below: (where, Z represents a nitrogen atom or CH, Y represents an uncondensed aromatic hydrocarbon group or condensed polycyclic hydrocarbon group, X1 represents O, S or Se, and X2 represents SH (or S−), Se−, a C1-4 alkyl or a morpholino group).

  一种标记剂，包括由下式（1）表示的多个核苷酸衍生物单元：（其中，Z表示氮原子或CH，Y表示未缩合的芳香烃基团或缩合的多环烃基团，X1表示O、S或Se，X2表示SH（或S−）、Se−、C1-4烷基或morpholino基团）。
• Biaryl modification of the 5′-terminus of one strand of a microRNA duplex induces strand specificity
  作者：Aya Ogata、Chihiro Furukawa、Kouhei Sakurai、Hideo Iba、Yukio Kitade、Yoshihito Ueno

  DOI：10.1016/j.bmcl.2010.10.077

  日期：2010.12

  MicroRNAs (miRNAs) are single-stranded non-coding RNAs composed of 20-23 nucleotides. They are initially transcribed in the nucleus as pri-miRNAs. After processing, one strand from the miRNA duplex (miR-5p/miR-3p duplex) is loaded onto the RNA-induced silencing complex (RISC) to produce a functional, mature miRNA that inhibits the expression of multiple target genes. In the case of some miRNAs, both strands can be equally incorporated into the RISC as single strands, and both strands can function as mature miRNAs. Thus, a technique for selective expression of miR-5p and miR-3p strands is required to identify distinct targets of miRNAs. In this Letter, we report the synthesis and properties of miRNA duplexes carrying biaryl units at the 5'-terminus of one strand. We found that incorporation of biaryl units at the 5'-terminus of one strand of miRNA duplexes induced strand specificity in these duplexes. Further, we succeeded in identifying endogenous mRNA targets for each strand of the duplex by using the biaryl-modified miRNA duplexes. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and properties of a novel molecular beacon containing a benzene-phosphate backbone at its stem moiety
  作者：Yoshihito Ueno、Akihiro Kawamura、Keiji Takasu、Shinji Komatsuzaki、Takumi Kato、Satoru Kuboe、Yoshiaki Kitamura、Yukio Kitade

  DOI：10.1039/b901631g

  日期：——

  This paper describes the synthesis and properties of a novel molecular beacon (MB) containing a benzene-phosphate backbone at its stem moiety. The fluorescence intensity of MBs was found to stabilize by the introduction of the benzene-phosphate backbone at its stem moiety. Furthermore, an MB containing the benzene-phosphate backbone was more resistant to DNase I (endonuclease) than an MB comprising natural DNA and 2′-O-methyl-RNA. These results indicate that the MB with the benzene-phosphate backbone is superior as a molecular beacon as compared to the MB composed of natural DNA and 2′-O-methyl-RNA.

  本文描述了一种新型分子信标（MB）的合成及其性能，该分子信标的茎部分含有苯基磷酸骨架。研究发现，随着苯基磷酸骨架的引入，MB的荧光强度得到了稳定。此外，含有苯基磷酸骨架的MB对DNase I（内切酶）的抗性强于由天然DNA和2′-O-甲基-RNA组成的MB。这些结果表明，含有苯基磷酸骨架的MB相较于由天然DNA和2′-O-甲基-RNA组成的MB更具优势。