1-methyl-3-(2,2,2-trichloroethoxysulfuryl)-3H-imidazol-1-ium triflate

• 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: 1-methyl-3-(2,2,2-trichloroethoxysulfuryl)-3H-imidazol-1-ium triflate
• 英文别名: 2,2,2-trichloroethoxysulfuryl-1-methylimidazole triflate；2,2,2-trichloroethylsulfuryl 2-methylimidazolium triflate；SMIS；2,2,2-Trichloroethyl 3-methylimidazol-3-ium-1-sulfonate;trifluoromethanesulfonate
• 化学式: CF₃O₃S*C₆H₈Cl₃N₂O₃S
• 分子量: 443.637
• InChiKey: RCNDUSSSXMVXGQ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.84
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-methyl-3-(2,2,2-trichloroethoxysulfuryl)-3H-imidazol-1-ium triflate 、 双丙酮半乳糖 在 N-甲基咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以87%的产率得到1:2,3:4-di-O-isopropylidene-6-O-trichloroethylsulfogalactose
  参考文献：
  名称：

  将2,2,2-三氯乙基保护的硫酸盐与亚磺酰基咪唑鎓盐一起引入单糖中，并应用于硫酸化碳水化合物的合成。

  摘要：

  DOI：

  10.1002/anie.200600153
• 作为产物：
  描述：

  1-(2,2,2-trichloroethoxysulfuryl)-imidazole 、 三氟甲烷磺酸甲酯 以 乙醚 为溶剂， 反应 3.0h， 以91%的产率得到1-methyl-3-(2,2,2-trichloroethoxysulfuryl)-3H-imidazol-1-ium triflate
  参考文献：
  名称：

  将2,2,2-三氯乙基保护的硫酸盐与亚磺酰基咪唑鎓盐一起引入单糖中，并应用于硫酸化碳水化合物的合成。

  摘要：

  DOI：

  10.1002/anie.200600153

文献信息

• Side reactions with 2,2,2-trichloroethoxysulfates during the synthesis of glycans
  作者：Kenya Matsushita、Yuta Sato、Shinji Funamoto、Jun-ichi Tamura

  DOI：10.1016/j.carres.2014.05.012

  日期：2014.9

  Protected sulfate groups may be used as an alternative tool to provide sulfate esters at hydroxyl and amino groups, particularly on complex glycans. We examined 2,2,2-trichloroethoxysulfation at the mono-, di-, and trihydroxyl groups of saccharide moieties to show regioselective sulfation. We found some side reactions including inter- and intramolecular nucleophilic reactions with 2,2,2-trichloroethoxysulfates

  受保护的硫酸盐基团可用作在羟基和氨基基团上提供硫酸酯的替代工具，特别是在复杂的聚糖上。我们检查了糖部分的单，二和三羟基处的2,2,2-三氯乙氧基硫酸化反应，以显示区域选择性的硫酸化作用。我们发现了一些副反应，包括与2,2,2-三氯乙氧基硫酸盐的分子间和分子内亲核反应。
• Sulfated liposaccharides inspired by telomerase inhibitor axinelloside A
  作者：Jie Guang、Zachary A. Rumlow、Lauren M. Wiles、Sloane O'Neill、Maciej A. Walczak

  DOI：10.1016/j.tetlet.2017.11.038

  日期：2017.12

  Sulfated liposaccharides are known inhibitors of telomerase and here we describe the synthesis of a series of sulfated liposaccharides inspired by the natural product axinelloside A, reported to act as an inhibitor of human telomerase. We established a robust and scalable synthetic route to galactosyl liposaccharides capitalizing on a series of regioselective acylation reactions with 2-decenoic acid

  硫酸化的脂糖是端粒酶的已知抑制剂，在这里我们描述了一系列天然产物axinelloside A激发的一系列硫酸化的脂糖的合成，据报道，该产物可作为人类端粒酶的抑制剂。我们利用2-癸烯酸和硫酸咪唑鎓酯的一系列区域选择性酰化反应，建立了一种健壮且可扩展的半乳糖基脂糖合成路线。
• CD1b Tetramers Identify T Cells that Recognize Natural and Synthetic Diacylated Sulfoglycolipids from Mycobacterium tuberculosis
  作者：Charlotte A. James、Krystle K.Q. Yu、Martine Gilleron、Jacques Prandi、Vijayendar R. Yedulla、Zuzanna Z. Moleda、Eleonora Diamanti、Momin Khan、Varinder K. Aggarwal、Josephine F. Reijneveld、Peter Reinink、Stefanie Lenz、Ryan O. Emerson、Thomas J. Scriba、Michael N.T. Souter、Dale I. Godfrey、Daniel G. Pellicci、D. Branch Moody、Adriaan J. Minnaard、Chetan Seshadri、Ildiko Van Rhijn

  DOI：10.1016/j.chembiol.2018.01.006

  日期：2018.4

  Mycobacterial cell wall lipids bind the conserved CD1 family of antigen-presenting molecules and activate T cells via their T cell receptors (TCRs). Sulfoglycolipids (SGLs) are uniquely synthesized by Mycobacterium tuberculosis, but tools to study SGL-specific T cells in humans are lacking. We designed a novel hybrid synthesis of a naturally occurring SGL, generated CD1b tetramers loaded with natural or synthetic SGL analogs, and studied the molecular requirements for TCR binding and T cell activation. Two T cell lines derived using natural SGLs are activated by synthetic analogs independently of lipid chain length and hydroxylation, but differentially by saturation status. By contrast, two T cell lines derived using an unsaturated SGL synthetic analog were not activated by the natural antigen. Our data provide a bioequivalence hierarchy of synthetic SGL analogs and SGL-loaded CD1b tetramers. These reagents can now be applied to large-scale translational studies investigating the diagnostic potential of SGL-specific T cell responses or SGL-based vaccines.
• <i>O</i>- and <i>N</i>-Sulfations of Carbohydrates Using Sulfuryl Imidazolium Salts
  作者：Laura J. Ingram、Ahmed Desoky、Ahmed M. Ali、Scott D. Taylor

  DOI：10.1021/jo9014112

  日期：2009.9.4

  A series of sulfuryl imidazolium salts (SISs) were prepared and examined as reagents for incorporating trichloroethyl-protected sulfate esters into carbohydrates. The SIS that contained a 1,2-dimethylimidazolium moiety (SIS 9) proved to be a superior sulfating compared to SISs bearing no alkyl groups or bulkier alkyl groups on the imidazolium ring. Difficult O-sulfations that required prolonged reaction times and a large excess of the SIS bearing a 1-methylimidazolium group (SIS 5) were achieved in high yield using less than half the amount of SIS 9 in less time. Certain N-sulfated compounds that were practically inaccessible using SIS 5 were obtained in excellent yield using SIS 9.
• Introduction of 2,2,2-Trichloroethyl-Protected Sulfates into Monosaccharides with a Sulfuryl Imidazolium Salt and Application to the Synthesis of Sulfated Carbohydrates
  作者：Laura J. Ingram、Scott D. Taylor

  DOI：10.1002/anie.200600153

  日期：2006.5.19