TFE*OTf | 1269657-45-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: TFE*OTf
• CAS: 1269657-45-5
• 化学式: CF₃O₃S*C₇H₁₀F₃N₂O₃S
• 分子量: 408.3
• InChiKey: PDMCDJORTKFRQL-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.34
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  109.38
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  TFE*OTf 、 双丙酮半乳糖 在 1,2-二甲基咪唑 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到Sulfuric acid (3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethyl ester 2,2,2-trifluoro-ethyl ester
  参考文献：
  名称：

  Preparation of trifluoroethyl- and phenyl-protected sulfates using sulfuryl imidazolium salts

  摘要：

  Sulfuryl imidazolium salts (SIS's), a new class of sulfating agents, were prepared bearing the trifluoroethyl (TFE) and phenyl groups, two functionalities that have been used for the protection of sulfate monoesters, by subjecting the corresponding sulfonyl imidazoles with methyl triflate. In contrast, SIS's bearing the electron donating neopentyl and isobutyl groups, two moieties that have also been used for the protection of sulfates, were found to be unstable and could not be isolated though SIS's bearing electron donating aryl groups, such as a p-methoxyphenyl or p-thiomethylphenyl group were readily prepared and are stable compounds. In most instances, TFE-protected phenolic and carbohydrate sulfates were obtained in good yield by reaction of the corresponding SIS's with steroids and carbohydrates. Phenyl-protected carbohydrates were also readily prepared using the corresponding SIS's. Those SIS's having a methyl group at the 2-position of the imidazole ring were, in general, superior sulfating agents to those, which lacked a methyl group at this position. The use of SIS's to prepare TFE-protected sulfates represents a significant improvement of the previous reported procedure, which involved treating unprotected sulfates with trifluorodiazoethane. The TFE protecting group was removed from steroidal sulfates and secondary sulfates in carbohydrates in high yields using NaN(3) in warm DMF, conditions that are less vigorous than those previously reported for removing this group. Deprotection of TFE-protected 6-sulfated carbohydrates using NaN3 in warm DMF proceeded in lower yields due to partial desulfation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.085
• 作为产物：
  描述：

  2,2,2-trifluoroethyl 2-methyl-1H-imidazole-1-sulfonate 、 三氟甲烷磺酸甲酯 以 乙醚 为溶剂， 反应 3.5h， 以91%的产率得到TFE*OTf
  参考文献：
  名称：

  Preparation of trifluoroethyl- and phenyl-protected sulfates using sulfuryl imidazolium salts

  摘要：

  Sulfuryl imidazolium salts (SIS's), a new class of sulfating agents, were prepared bearing the trifluoroethyl (TFE) and phenyl groups, two functionalities that have been used for the protection of sulfate monoesters, by subjecting the corresponding sulfonyl imidazoles with methyl triflate. In contrast, SIS's bearing the electron donating neopentyl and isobutyl groups, two moieties that have also been used for the protection of sulfates, were found to be unstable and could not be isolated though SIS's bearing electron donating aryl groups, such as a p-methoxyphenyl or p-thiomethylphenyl group were readily prepared and are stable compounds. In most instances, TFE-protected phenolic and carbohydrate sulfates were obtained in good yield by reaction of the corresponding SIS's with steroids and carbohydrates. Phenyl-protected carbohydrates were also readily prepared using the corresponding SIS's. Those SIS's having a methyl group at the 2-position of the imidazole ring were, in general, superior sulfating agents to those, which lacked a methyl group at this position. The use of SIS's to prepare TFE-protected sulfates represents a significant improvement of the previous reported procedure, which involved treating unprotected sulfates with trifluorodiazoethane. The TFE protecting group was removed from steroidal sulfates and secondary sulfates in carbohydrates in high yields using NaN(3) in warm DMF, conditions that are less vigorous than those previously reported for removing this group. Deprotection of TFE-protected 6-sulfated carbohydrates using NaN3 in warm DMF proceeded in lower yields due to partial desulfation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.085

文献信息

• Synthesis of <i>Mycobacterium tuberculosis</i> Sulfolipid-3 Analogues and Total Synthesis of the Tetraacylated Trehaloglycolipid of <i>Mycobacterium paraffinicum</i>
  作者：Vikram A. Sarpe、Santanu Jana、Suvarn S. Kulkarni

  DOI：10.1021/acs.orglett.5b03300

  日期：2016.1.4

  3-diacyl trehaloses to access Mycobacterium tuberculosis sulfolipid SL-3 and related 2,3,6-triester glycolipid analogues is reported for the first time. The methodology was successfully extended to achieve the first total synthesis of the tetraacylated trehalose glycolipid from Mycobacterium paraffinicum. The corresponding 2,3,6′-triesters trehalose glycolipids were also synthesized starting from the common

  首次报道了一种新颖的方法，用于2,3-二酰基海藻糖的区域选择性O6酰化以进入结核分枝杆菌硫脂SL-3和相关的2,3,6-三酯糖脂类似物。该方法已成功地扩展到从石蜡分枝杆菌中首次合成了四酰基化海藻糖糖脂。相应的2,3,6'-三酯海藻糖糖脂也从常见的2,3-二酰基海藻糖开始合成。这些合成的糖脂是结核病血清诊断和疫苗开发的潜在候选者。
• (<i>E</i>)- and (<i>Z</i>)-Stereodefined Enol Sulfate Esters Derived from α-Aryl Aldehydes: Stereocomplementary Synthesis of Styryl Sulfate Natural Products
  作者：Shuai Yu、Feng Li、Sanghee Kim

  DOI：10.1021/acs.joc.7b00868

  日期：2017.7.7

  of enol sulfate esters from α-aryl aldehydes is described. This method involved the stereocontrolled enolization of a carbonyl group with DBU or t-BuOK followed by trapping with a reactive sulfuryl imidazolium salt, providing the corresponding styryl enol sulfate esters in good to excellent yields and stereoselectivities. This method was applied to the first total synthesis of the enol sulfate natural

  描述了一种由α-芳基醛立体选择性地形成烯醇硫酸酯的方法。该方法涉及用DBU或t- BuOK对羰基进行立体控制的烯醇化，然后用反应性硫基咪唑鎓盐进行捕集，从而以良好或极好的收率和立体选择性提供相应的苯乙烯基烯醇硫酸酯。该方法以立体互补的方式应用于硫酸烯醇天然产物的第一次全合成。
• Rapid and efficient chemoselective and multiple sulfations of phenols using sulfuryl imidazolium salts
  作者：Scott D. Taylor、Ahmed Desoky

  DOI：10.1016/j.tetlet.2011.04.080

  日期：2011.6

  Phenolic sulfates protected with a trichloroethyl or trifluoroethyl group were rapidly and efficiently obtained by reacting phenols with sulfuryl imidazolium salts in the presence of DBU. Phenolic hydroxyl groups could be sulfated in good yield in the presence of aliphatic hydroxyl groups and multiple sulfations were also readily achieved. (C) 2011 Elsevier Ltd. All rights reserved.