tert-butyldimethylsilyl trifluoromethanesulfonate | 124156-70-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: tert-butyldimethylsilyl trifluoromethanesulfonate
• 英文别名: (tert-butyldimethylsilyl)methanesulfonate；tert-butyldimethylsilyl triflate；TBSOTf；tert-butyl(dimethyl)silyl methanesulfonate；tert-Butyldimethylsilyl methanesulfonate；[tert-butyl(dimethyl)silyl] methanesulfonate
• CAS: 124156-70-3
• 化学式: C₇H₁₈O₃SSi
• 分子量: 210.37
• InChiKey: QCEPCNPORJNRJB-UHFFFAOYSA-N

物化性质

• 沸点：
  236.7±9.0 °C(Predicted)
• 密度：
  1.014±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  12
• 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：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyldimethylsilyl trifluoromethanesulfonate 在 2,6-二甲基吡啶 、 silver nitrate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 生成 2-<(E)-(4S,6R)-4,6-bis(tert-butyldimethylsilyloxy)-1,5,5-trimethyl-9-<(2S,4S,5R)-tetrahydro-5-methyl-4-(triisopropylsilyloxy)-2-furanyl>-8-nonenyl>-1,3-dithiane
  参考文献：
  名称：

  Total synthesis of aplasmomycin

  摘要：

  DOI：

  10.1021/ja00388a074
• 作为试剂：
  描述：

  4-[4-bromo-5-(4-fluorophenyl)-3-methyl-1H-pyrazol-1-yl]butan-2-one 、 lead(IV) tetraacetate 在 tert-butyldimethylsilyl trifluoromethanesulfonate 、 三乙胺 、 potassium hydrogencarbonate 、 四丁基氟化铵 作用下， 以 甲苯 、 四氢呋喃 为溶剂， 反应 4.5h， 生成
  参考文献：
  名称：

  PYRAZOLE COMPOUNDS

  摘要：

  本发明涉及其中每个符号如规范中定义的。该化合物具有优越的矿物皮质激素受体拮抗作用，并可用作通过矿物皮质激素受体激活介导的疾病或病况的预防或治疗剂。

  公开号：

  US20100094000A1

文献信息

• Preparation of chiral phosphorus, sulfur and selenium containing 2-aryloxazolines
  作者：Markus Peer、Johannes C. de Jong、Matthias Kiefer、Thomas Langer、Heiko Rieck、Heico Schell、Peter Sennhenn、Jürgen Sprinz、Henning Steinhagen、Burkhard Wiese、Günter Helmchen

  DOI：10.1016/0040-4020(96)00267-0

  日期：1996.5

  synthetic amino alcohols. For oxazoline formation three procedures were employed: (i) one pot condensation with a 2-halobenzoic acid, (ii) ZnCl2 catalyzed condensation with a 2-halobenzonit-rile, and (iii) a three step sequence via a 2-halobenzamide and a tosylate or chloride. Phosphinooxazolines containing stereogenic phosphorus were prepared by either diastereoselective nucleophilic substitution of halogenide

  由市售或合成的氨基醇制备一系列对映体纯的2- [2-（二芳基膦基）芳基]-恶唑啉。对于恶唑啉的形成，采用了三种程序：（i）与2-卤代苯甲酸一锅缩合，（ii）ZnCl 2与2-卤代苯甲腈-苯胺催化缩合，和（iii）通过2-卤代苯甲酰胺的三步顺序和甲苯磺酸盐或氯化物。通过非对映选择性亲核取代Ar 1 Ar 2 PC1的卤化物或通过LiPAr 1 Ar 2亲核芳族取代制备含有立体异构磷的膦恶唑啉。另外，制备了硫和硒类似物。
• Total Synthesis of (+)-Manzamine A
  作者：Tatsuya Toma、Yoichi Kita、Tohru Fukuyama

  DOI：10.1021/ja103721s

  日期：2010.8.4

  A novel synthetic route to (+)-manzamine A was developed. It highlights an amazingly efficient construction of a highly strained 15-membered ring across a cyclohexenone ring with the aim of installing the requisite functionalities in a completely stereocontrolled manner. Other key features include a stereoselective Diels-Alder reaction of an optically active butenolide, construction of the 15-membered

  开发了一种新的 (+)-manzamine A 合成路线。它突出了环己烯酮环上高度应变的 15 元环的惊人高效构建，目的是以完全立体控制的方式安装必要的功能。其他关键特征包括旋光性丁烯内酯的立体选择性 Diels-Alder 反应、通过硝基酰胺的分子内光信反应构建 15 元环、[3,3]-氰酸烯丙酯的 [3,3]-σ 重排以立体选择性地引入氮官能团空间拥挤的位置，以及在不稳定官能团存在下的闭环复分解。
• Hydroxyselanylation of acyloxycyclohex-3-enes
  作者：J.B. Sweeney、Alan F. Haughan、J.R. Knight、Smita Thobhani

  DOI：10.1016/j.tet.2006.12.035

  日期：2007.3

  In contrast to the corresponding hydroxyiodination reactions, the reaction of acetoxycyclohex-2-ene 1 with N-PSP in the presence of water shows little regiocontrol, but is highly diastereoselective. However, the same reaction of the (R)-phenylglycinate derivative of (±)-cyclohexen-3-ol is highly diastereoselective, and regioselective. A hydrogen-bonding interaction is proposed to rationalize these

  与相应的羟基碘化反应相反，在水的存在下，乙酰氧基环己-2-烯1与N -PSP的反应几乎没有区域控制性，但是具有非对映选择性。然而，（±）-环己烯-3-醇的（R）-苯基甘氨酸酯衍生物的相同反应是高度非对映选择性和区域选择性的。提出氢键相互作用以合理化这些不同的选择性。
• Development of new simple molecular probes of DNA bulged structures
  作者：Ziwei Xiao、Lizzy S. Kappen、Irving H. Goldberg

  DOI：10.1016/j.bmcl.2006.03.006

  日期：2006.6

  NCSi-gb is a neocarzinostatin chromophore (NCS-chrom) metabolite which binds strongly to certain two-base DNA bulges. Compared with previously reported NCSi-gb analogues, a new analogue with a different aminoglycoside position was synthesized, and it showed strong fluorescence and improved binding and sequence selectivity to DNA bulges. The N-dimethylated form of this analogue had a similar binding

  NCSi-gb是新碳抑制素发色团（NCS-chrom）代谢产物，可与某些两碱基DNA凸起牢固结合。与以前报道的NCSi-gb类似物相比，合成了具有不同氨基糖苷位置的新类似物，它显示出强荧光，并改善了对DNA凸起的结合和序列选择性。该类似物的N-二甲基化形式具有相似的结合模式，并且竞争性地抑制了NCS-chrom的凸起特异性切割。
• Synthesis and biological activities of new 1α,25-dihydroxy-19-norvitamin D3 analogs with modifications in both the A-ring and the side chain
  作者：Masato Shimizu、Yukiko Miyamoto、Emi Kobayashi、Mika Shimazaki、Keiko Yamamoto、Wolfgang Reischl、Sachiko Yamada

  DOI：10.1016/j.bmc.2006.01.061

  日期：2006.6

  In a series of studies on structure-activity relationships of 2-substituted 19-norvitamin D analogs, we found that 1 alpha,25-dihydroxy-19-norvitamin D-3 analogs with 2 beta-hydroxyethoxy or 2E-hydroxyethylidene moieties show strong binding affinity for the vitamin D receptor (VDR) as well as marked transcriptional activity. To further examine the effects of side chain structure on the activity of 2-substituted 19-norvitamin D analogs, we have synthesized new 19-norvitamin D3 analogs with modifications in both the A-ring at the C(2) position and the side chain. The side chains of these analogs contained a double bond between C(22) and C(23) or an oxygen atom at C(22). The biological activity of the analogs was evaluated in vitro. All the side chain-modified analogs were less active than 1 alpha,25-dihydroxyvitamin D-3 1e and the parent compounds 3-6e possessing a natural 20R-configuration in binding to the VDR, but, except for the (20R)-22-oxa analogs 3-6d, were significantly more potent in transcriptional activity. Of the side-chain-modified analogs 4 and 5, the 2 beta-hydroxyethoxy- and 2E-hydroxyethylidene-22,24-diene-24a,26a,27a-trihorno analogs showed markedly higher transcriptional activity (25- and 17.5-fold, respectively) compared with le. Elongation of the side chain at the C-24, C-26, and C-27 positions and introduction of a 22,24-diene moiety strongly increased transcriptional activity, as seen in the 20-epi analogs 3-6f. (c) 2006 Elsevier Ltd. All rights reserved.