bis(trimethylsilyloxy)(cyclododecyloxy)silyl chloride | 263136-62-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: bis(trimethylsilyloxy)(cyclododecyloxy)silyl chloride
• 英文别名: Trisiloxane, 3-chloro-3-(cyclododecyloxy)-1,1,1,5,5,5-hexamethyl-；chloro-cyclododecyloxy-bis(trimethylsilyloxy)silane
• CAS: 263136-62-5
• 化学式: C₁₈H₄₁ClO₃Si₃
• 分子量: 425.231
• InChiKey: VUHIEZPSODGSGB-UHFFFAOYSA-N

物化性质

• 沸点：
  390.1±25.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.05
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  bis(trimethylsilyloxy)(cyclododecyloxy)silyl chloride 在 咪唑 、 四氮唑 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 19.3h， 生成 2'-O-(bis(2-acetoxyethoxy)methyl)-5'-O-[bis(trimethylsiloxy)(cyclododecyloxy)silyl]-4-N-(4,4'-dimethoxytrityl)cytidine 3'-(N,N-diisopropyl)methoxyphosphoramidite
  参考文献：
  名称：

  Synthesis of the Ribosomal P-Site Substrate CCA-pcb

  摘要：

  CCA-pcb (cytidylyl-(3'5')-cytidylyl-(3'5')-3'(2')-O-(N-(6-D-(+)-biotinoylaminohexanoyl)-L-phenylalanyl)adenosine), a ribosomal P-site substrate, was synthesized by phosphoramidite chemistry in 26 steps with an overall yield of 18%, starting from biotin. The synthesis relies on the judicious selection of orthogonal silyl protecting groups for the 5'-hydroxyls and acid-labile protecting groups (DMTr, AcE, and MeE) at other reactive sites to ensure the intactness of the labile ester. Both X-esterification and nucleotide coupling were accomplished by in situ activation with imidazolium ions.

  DOI：

  10.1021/ol052484f

文献信息

• Synthesis of Isotopically Labeled P-Site Substrates for the Ribosomal Peptidyl Transferase Reaction
  作者：Minghong Zhong、Scott A. Strobel

  DOI：10.1021/jo702070m

  日期：2008.1.1

  (cytidine), 93% for 2‘/3‘-18O (adenosine), and 64% for 1-18O (Phe). A new synthesis of highly enriched [1-18O2]phenylalanine has been developed. The synthesis of [3‘-18O]adenosine was improved by Lewis acid aided regioselective ring opening of the epoxide and by an economical SN2−SN2 method with high isotopic enrichment (93%). Such substrates are valuable for studies of the ribosomal peptidyl transferase reaction

  核糖体 P 位点底物的同位素异构体，即三核苷酸肽偶联物 CCA-pcb（Zhong, M.；Strobel, SA Org. Lett. 2006 , 8 , 55-58），已通过 26-35 个步骤设计和合成。这些包括氨基酸的 α-氢、羰基碳和羰基氧、腺苷的 O2' 和 O3' 处的单个同位素取代，以及两个胞苷的 N3 和 N4 中的远程标记。这些同位素是通过将胞苷酰-(3',5')-胞苷亚磷酰胺同位素作为常见的合成中间体与同位素取代的 A-Phe-cap-生物素 (A-pcb) 偶联来合成的。1- 13 C (Phe)、2- 2 H (Phe) 和 3,4- 15 N 2的同位素富集率高于 99%(胞苷)，2'/3'- 18 O (腺苷)为 93% ，1- 18 O (Phe)为 64% 。已开发出一种高富集 [1- 18 O 2 ] 苯丙氨酸的新合成方法。[3'- 18 O]腺苷的合
• SITE SPECIFIC INCORPORATION OF 6-AZAURIDINE INTO THE GENOMIC HDV RIBOZYME ACTIVE SITE
  作者：Adegboyega K. Oyelere、Scott A. Strobel

  DOI：10.1081/ncn-100107196

  日期：2001.12.31

  histidine-like N3 pKa. into the genomic HDV ribozyme active site by 2'-O-ACE oligoribonucleotide protection chemistry. The resulting ribozymes were analyzed for their ability to undergo the HDV ribozyme cis-cleavage reaction. Incorporation of n6U at nucleotide position 75 did not restore ribozyme function compared to the U75 mutant. This suggests that the HDV ribozyme reaction mechanism involves more than positioning

  提出HDV核酶通过质子转移机制催化其自身裂解反应，其中C75的N3充当一般酸。从C75到U的突变将N3 pKa从大约4提高到几乎10。这消除了所有酶的活性。为了测试具有中性pKa的U类似物是否可以恢复核酶功能，我们引入了6-氮杂尿苷（n6U），尿苷类似物与组氨酸样N3 pKa。通过2'-O-ACE寡核糖核苷酸保护化学将其导入基因组HDV核酶活性位点。分析所得核酶进行HDV核酶顺式裂解反应的能力。与U75突变体相比，在核苷酸75位上掺入n6U不能恢复核酶功能。
• Preparation and Analysis of Oligonucleotides Containing the C4‘-Oxidized Abasic Site and Related Mechanistic Probes
  作者：Jaeseung Kim、Cortney R. Kreller、Marc M. Greenberg

  DOI：10.1021/jo0512249

  日期：2005.9.1

  The C4‘-oxidized abasic site (C4-AP) is produced by a variety of DNA damaging agents. This alkali labile lesion can exist in up to four diastereomeric cyclic forms, in addition to the acyclic keto-aldehyde. Synthetic oligonucleotides containing the lesion were prepared from a stable photochemical precursor. Chemical integrity of the lesion containing oligonucleotides was probed using phosphodiesterase

  C4'氧化的无碱基位点（C4-AP）是由多种DNA破坏剂产生的。除了无环酮醛外，这种对碱不稳定的病变还可以以多达四种非对映异构的环状形式存在。由稳定的光化学前体制备含有病变的合成寡核苷酸。使用磷酸二酯酶的不稳定性来探测含有病变的寡核苷酸的化学完整性。由光不稳定前体的单个非对映异构体释放的单体病变的3'，5'-磷酸二酯的分析为11 H NMR表明半缩醛和/或半缩酮的异构化是快速的。还描述了含有构型稳定的C4-AP类似物的寡核苷酸的合成和表征，所述寡核苷酸用作破译C4'-氧化的无碱基病变的生物化学和生物学作用的结构基础的机械探针。
• Synthesis and Deprotection of Oligonucleotides under Aprotic Conditions
  作者：Tongqian Chen、Jiasheng Fu、Marc M. Greenberg

  DOI：10.1021/ol006604p

  日期：2000.11.1

  [GRAPHICS]Oligonucleotides containing an alkali labile nucleotide are synthesized and deprotected using a synthetic method that eliminates the use of Bronsted acid and base. The development of a new family of exocyclic amine protecting groups is an integral component of this approach.
• Synthesis and Characterization of Oligonucleotides Containing the C4′-Oxidized Abasic Site Produced by Bleomycin and Other DNA Damaging Agents
  作者：Jaeseung Kim、Jun Mo Gil、Marc M. Greenberg

  DOI：10.1002/anie.200352102

  日期：2003.12.8