(tert-butyldimethylsilyloxy)methyl chloride | 119451-80-8

• 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: (tert-butyldimethylsilyloxy)methyl chloride
• 英文别名: tert-Butyldimethylsiloxychloromethane；tert-butyl-(chloromethoxy)-dimethylsilane
• CAS: 119451-80-8
• 化学式: C₇H₁₇ClOSi
• 分子量: 180.75
• InChiKey: IYLFKXATVSYTQV-UHFFFAOYSA-N

物化性质

• 沸点：
  157.2±13.0 °C(Predicted)
• 密度：
  0.914±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (tert-butyldimethylsilyloxy)methyl chloride 在 正丁基锂 、 硫化氢 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以92%的产率得到[(tert-butyldimethylsilyl)oxy]methanethiol
  参考文献：
  名称：

  [(tert-Butyldimethylsilyl)oxy]methanethiol and [(tert-butyldiphenylsilyl)oxy]methanethiol—nucleophilic protected H2S equivalents

  摘要：

  [(tert-Butyldimethylsilypoxy]methanethiol [HSCH2OSiMe2Bu-t] is a nucleophilic reagent for introduction of a protected bivalent sulfur; this reagent is complementary to the electrophilic reagent p-MeC6H4SO2SCH2OSiMe2Bu-t. The thiol is prepared by the action of HSLi on tert-butyl(chloromethoxy) dimethylsilane [CICH2OSiMe2Bu-t] and it reacts with alkyl bromides to give protected thiols. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.079
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 4-二甲氨基吡啶 、 磺酰氯 、 三乙胺 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.67h， 生成 (tert-butyldimethylsilyloxy)methyl chloride
  参考文献：
  名称：

  Gundersen, Lise-Lotte; Benneche, Tore; Undheim, Kjell, Acta Chemica Scandinavica, 1989, vol. 43, # 7, p. 706 - 709

  摘要：

  DOI：

文献信息

• The Total Synthesis of Corallopyronin A and Myxopyronin B
  作者：Andreas Rentsch、Markus Kalesse

  DOI：10.1002/anie.201206560

  日期：2012.11.5

  Leading the way: The synthesis of natural products with new biological targets is one of the driving forces for the development of new antibiotics. The synthesis of the two secondary metabolites corallopyronin and myxopyronin (see picture) have been achieved, which are prominent leads for the inhibition of bacterial RNA polymerase.

  引领潮流：合成具有新生物靶标的天然产物是开发新抗生素的驱动力之一。已经实现了两种次生代谢产物珊瑚红素和粘氧嘧啶的合成（见图），这是抑制细菌RNA聚合酶的重要线索。
• [[(<i>tert</i>-Butyl)dimethylsilyl]oxy]methyl Group for Sulfur Protection
  作者：Lihong Wang、Derrick L. J. Clive

  DOI：10.1021/ol2002573

  日期：2011.4.1

  aliphatic thiols can be protected by reaction with t-BuMe2SiOCH2Cl in DMF in the presence of a base (2,6-lutidine or proton sponge); the resulting t-BuMe2SiOCH2SR or t-BuMe2SiOCH2SAr are deprotected by sequential treatment with Bu4NF and I2 to give symmetrical disulfides. Another mode of deprotection involves reaction with a sulfenyl chloride; this process gives an unsymmetrical disulfide and was examined

  芳族和脂族硫醇可以通过与保护吨-BuMe 2的SiOCH 2氯在DMF中，在碱（2,6-二甲基吡啶或质子海绵）的存在; 所得吨-BuMe 2的SiOCH 2 SR或吨-BuMe 2的SiOCH 2 SAR通过用布顺序处理脱保护4 NF和我2，得到对称的二硫化物。脱保护的另一种方式涉及与亚磺酰氯反应。该过程产生不对称的二硫键，并用Me（CH 2）11 SCH 2 OSiMe 2 Bu-t和三个亚磺酰氯。
• [EN] MODIFIED NUCLEIC ACID MOLECULES AND USES THEREOF<br/>[FR] MOLÉCULES D'ACIDE NUCLÉIQUE MODIFIÉES ET LEURS UTILISATIONS
  申请人：MODERNA THERAPEUTICS INC

  公开号：WO2014093924A1

  公开（公告）日：2014-06-19

  The present disclosure provides modified nucleosides, nucleotides, and nucleic acids, and methods of using them.

  本公开提供了经修改的核苷、核苷酸和核酸，以及它们的使用方法。
• Asymmetric Total Synthesis of Epolactaene
  作者：Yujiro Hayashi、Koichi Narasaka

  DOI：10.1246/cl.1998.313

  日期：1998.4

  The first asymmetric total synthesis of epolactaene, a neuritogenic compound, was accomplished in 16 steps and its absolute stereochemistry was determined.

  首个不对称全合成的神经生长因子化合物epolactaene在16个步骤中完成，并且其绝对立体化学得到了确定。
• DNA adducts of aristolochic acid II: total synthesis and site-specific mutagenesis studies in mammalian cells
  作者：Sivaprasad Attaluri、Radha R. Bonala、In-Young Yang、Mark A. Lukin、Yujing Wen、Arthur P. Grollman、Masaaki Moriya、Charles R. Iden、Francis Johnson

  DOI：10.1093/nar/gkp815

  日期：2010.1

  Aristolochic acids I and II (AA-I, AA-II) are found in all Aristolochia species. Ingestion of these acids either in the form of herbal remedies or as contaminated wheat flour causes a dose-dependent chronic kidney failure characterized by renal tubulointerstitial fibrosis. In ∼50% of these cases, the condition is accompanied by an upper urinary tract malignancy. The disease is now termed aristolochic acid nephropathy (AAN). AA-I is largely responsible for the nephrotoxicity while both AA-I and AA-II are genotoxic. DNA adducts derived from AA-I and AA-II have been isolated from renal tissues of patients suffering from AAN. We describe the total synthesis, de novo, of the dA and dG adducts derived from AA-II, their incorporation site-specifically into DNA oligomers and the splicing of these modified oligomers into a plasmid construct followed by transfection into mouse embryonic fibroblasts. Analysis of the plasmid progeny revealed that both adducts blocked replication but were still partly processed by DNA polymerase(s). Although the majority of coding events involved insertion of correct nucleotides, substantial misincorporation of bases also was noted. The dA adduct is significantly more mutagenic than the dG adduct; both adducts give rise, almost exclusively, to misincorporation of dA, which leads to AL-II-dA→T and AL-II-dG→T transversions.

  马兜铃酸 I 和 II（AA-I、AA-II）存在于所有马兜铃属植物中。无论是以草药的形式还是以被污染的小麦粉的形式摄入这些酸，都会导致以肾小管间质纤维化为特征的剂量依赖性慢性肾衰竭。在这些病例中，50%的病例伴有上尿路恶性肿瘤。这种疾病现在被称为马兜铃酸肾病（AAN）。肾毒性主要由 AA-I 引起，而 AA-I 和 AA-II 都具有遗传毒性。从 AAN 患者的肾组织中分离出了 AA-I 和 AA-II 的 DNA 加合物。我们介绍了从 AA-II 中提取的 dA 和 dG 加合物的全合成、特异性位点掺入 DNA 寡聚物以及将这些修饰过的寡聚物拼接到质粒构建体中并转染到小鼠胚胎成纤维细胞中的过程。对质粒后代的分析表明，这两种加合物都能阻止复制，但仍能被 DNA 聚合酶部分处理。虽然大多数编码事件都涉及正确核苷酸的插入，但也发现了大量碱基的错误插入。dA 加合物的致突变性明显高于 dG 加合物；两种加合物几乎都会引起 dA 的错结合，从而导致 AL-II-dA→T 和 AL-II-dG→T 的转换。