Tert-butyldimethylsilyl trifluoromethanesulfonate

Base Information

• Chemical Name: Tert-butyldimethylsilyl trifluoromethanesulfonate
• CAS No.: 69739-34-0
• Molecular Formula: C7H15F3O3SSi
• Molecular Weight: 264.341
• Hs Code.: 29310095
• European Community (EC) Number: 274-102-0
• UNII: EE45S257MT
• DSSTox Substance ID: DTXSID50220034
• Nikkaji Number: J267.418A
• Wikidata: Q72503031
• Mol file: 69739-34-0.mol

Synonyms:69739-34-0;Tert-butyldimethylsilyl trifluoromethanesulfonate;Trifluoromethanesulfonic Acid tert-Butyldimethylsilyl Ester;TBDMS triflate;t-Butyldimethylsilyl triflate;tert-Butyldimethylsilyl Triflate;tert-Butyldimethylsilyl trifluoromethanesulphonate;C7H15F3O3SSi;TBDMS-OTf;[tert-butyl(dimethyl)silyl] trifluoromethanesulfonate;tert-Butyldimethylsilyltrifluoromethanesulfonate;t-Butylmethylsilyl triflate;Methanesulfonic acid, trifluoro-, (1,1-dimethylethyl)dimethylsilyl ester;t-Butyldimethylsilyltrifluoromethanesulfonate;t-butyldimethylsilyl trifluoromethanesulfonate;EINECS 274-102-0;MFCD00000405;TBDMS-triflate;TBS Triflate;TBSOTf;TBDMSOTf;TBS-OTf;Silane TBM2 triflate;t-butyldimethylsilyltriflate;SCHEMBL38009;tert-butyldimethylsilyltriflate;tertbutyldimethylsilyl triflate;tert-butyl-dimethylsilyltriflate;EE45S257MT;Trifluoromethanesulfonicacidtert-butyldimethylsilylester;Trifluoromethanesulfonic acid tert-butyldimethylsilylester;DTXSID50220034;tert-Butyldimethylsilanyl triflate;AMY42272;BCP11360;CS-B0889;AKOS005063793;CS-O-10906;SB40842;AS-40537;BP-13052;BP-31181;FT-0600865;t-butyl-dimethylsilyltrifluoromethanesulfonate;t-butyldimethylsilyltrifluoromethane sulfonate;T1525;tert-butyldimethylsilyltrifluormethansulfonate;t-butyldimethylsilyl trifluoromethane sulfonate;t-Butyldimethylsilyl trifluoromethanesulphonate;tertbutyldimethylsilyl trifluoromethanesulfonate;EN300-128285;tert-butyl-dimethylsilyl-trifluoromethylsulfonate;tert-butyldimehylsilyltrifluoromethane sulfonate;tert-butyldimethylsilyl trifluormethanesulfonate;tert-Butyldimethylsilyl trifluoromethylsulfonate;tert-butyldimethylsilyl trifluromethane sulfonate;tert-butyldimethylsilyl trifluromethanesulfonate;tert-butyldimethylsilyltrifluoromethane sulfonate;t-butyl(dimethyl)silyl-trifluoromethane-sulfonate;tert-butyl dimethylsilyl trifluoromethanesulfonate;tert-butyldimethylsilyl trifluorome-thanesulfonate;tert-butyldimethylsilyl trifluoromethane sulfonate;tert-butyldimethylsilyl trifluoromethane-sulfonate;A934579;tert-butyl dimethylsilyl trifluoromethane sulfonate;tert-butyl(dimethyl)silyl trifluoromethanesulfonate;tert-butyl-dimethylsilyl trifluoromethanesulphonate;Q-201799;tert-butyl(dimethyl)silyl trifluoromethanesulphonate;tert-Butyldimethylsilyl trifluoromethanesulfonate, 98%;Trifluoromethanesulfonic acid t-butyldimethylsilyl ester;Trifluoromethanesulfonic acid-tert.-butyldimethylsilylester;tert-Butyldimethylsilyl trifluoromethanesulfonate, reagentgrade;(1,1-Dimethylethyl)dimethylsilyl 1,1,1-trifluoromethanesulfonate;tert-Butyldimethylsilyl trifluoromethanesulfonate, reagent grade, 98%;tert-Butyldimethylsilyl trifluoromethanesulfonate, purum, >=98.0% (T);1,1,1-trifluoro-methanesulfonic acid, (1,1-dimethylethyl)dimethylsilyl ester;Methanesulfonic acid, 1,1,1-trifluoro-, (1,1-dimethylethyl)dimethylsilyl ester;tert-Butyldimethylsilyl trifluoromethanesulfonate, for GC derivatization, >=98.0% (T)

Chemical Property of Tert-butyldimethylsilyl trifluoromethanesulfonate

Chemical Property:

• Appearance/Colour: clear colorless to yellow fuming liquid
• Vapor Pressure: 0.00137mmHg at 25°C
• Melting Point: <0oC
• Refractive Index: n20/D 1.385(lit.)
• Boiling Point: 182.4 °C at 760 mmHg
• Flash Point: 73.4 °C
• PSA: 51.75000
• Density: 1.181 g/cm³
• LogP: 3.93860
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Slightly miscible with chloroform.
• Water Solubility.: DECOMPOSES
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 264.04632653
• Heavy Atom Count: 15
• Complexity: 321

Purity/Quality:

99% ^*data from raw suppliers

tert-Butyldimethylsilyl trifluoromethanesulfonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, C
• Hazard Codes: C,F
• Statements: 10-34-37
• Safety Statements: 26-36/37/39-45-25-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F
• Physical properties: bp 60°C/7 mmHg; colorless oil, d 1.151 g cm?3. Solubility: sol most organic solvents such as pentane, CH2Cl2, etc.
• Uses: TrifluoroMethanesulfonic acid tert-butyldiMethylsilyl ester is a highly reactive silylating agent and lewis acid capable of converting primary, secondary and tertiary alcohols to their respectctive TBDMS. TrifluoroMethanesulfonic acid tert-butyldiMethylsilyl ester is also used to covert ketones and lactones into their enol silyl ethers. t-Butyldimethylsilyl Trifluoromethanesulfonate is used as a highly reactive silylating agent and Lewis acid capable of converting primary, secondary, and tertiary alcohols1b to the corresponding TBDMS ethers, and converting ketones and lactones, into their enol silyl ethers; promoting conjugate addition of alkynylzinc compounds and triphenylphosphine5 to α,β-enones; activation of chromones in [4 + 2] cycloaddition reactions;rearrangement of allylic tributylstannyl silyl ethers; activation of pyridine rings toward Grignard reagents and transalkylation of tertiary amine N-oxides;and transformation of N-t-butoxycarbonyl groups into N-alkoxycarbonyl groups. tert-Butyldimethylsilyl trifluoromethanesulfonate is involved in the introduction of a bulky tert-butyl dimethylsilyl group onto a cis-bis(alkenyl)oxirane used in Cope rearrangement. It is associated with a thiolane and promotes the chalcogenide-Morita-Baylis-Hillman reaction. Further, it is used as a highly reactive silylating agent. In addition to this, it is used to prepare enol silyl ethers by reacting with ketones and lactones.

Technology Process of Tert-butyldimethylsilyl trifluoromethanesulfonate

There total 12 articles about Tert-butyldimethylsilyl trifluoromethanesulfonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

trifluorormethanesulfonic acid (1493-13-6) + tert-butyldimethylsilyl chloride (18162-48-6) → t-butyldimethylsiyl triflate (69739-34-0)

Guidance literature:

at 60 ℃; for 16h;

Reference yield: 90.0%

trifluorormethanesulfonic acid (1493-13-6) + tert-butyldimethylsilane (29681-57-0) → t-butyldimethylsiyl triflate (69739-34-0)

Guidance literature:

at 40 ℃; for 0.25h; addition with ice-cooling;

DOI:10.1016/S0040-4039(00)95140-2

Reference yield: 66.0%

2-(trimethylsilyl)propene (18163-07-0) + trifluorormethanesulfonic acid (1493-13-6) → trimethylsilyl trifluoromethanesulfonate (27607-77-8) + t-butyldimethylsiyl triflate (69739-34-0)

Guidance literature:

In pentane; at 0 ℃; for 0.166667h; Yield given;

DOI:10.1016/S0040-4039(00)99052-X

upstream raw materials:

2-(trimethylsilyl)propene

trifluorormethanesulfonic acid

tert-butyldimethylsilane

tert-butyldimethylsilyl chloride

Downstream raw materials:

4'ξ-[(tert-butyl-dimethyl-silanyloxy)-methyl]-2'-cyclohexyl-3β-methoxy-(5α,16β,17β)-tetrahydro-androstano[17,16-e][1,2]oxazine-3'ξ-carbonitrile

4'ξ-[(tert-butyl-dimethyl-silanyloxy)-methyl]-2'-cyclohexyl-3β-methoxy-(5α,16β,17β)-tetrahydro-androstano[16,17-e][1,2]oxazine-3'ξ-carbonitrile

3β-acetoxy-4'ξ-[(tert-butyl-dimethyl-silanyloxy)-methyl]-2'-cyclohexyl-(5α,16β,17β)-tetrahydro-androstano[16,17-e][1,2]oxazine-3'ξ-carbonitrile

Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester

Refernces

Rapid construction of [5-6-7] tricyclic ring skeleton of calyciphylline alkaloid daphnilongeranin B

10.1021/ol200312q

The research focuses on the rapid construction of the [5-6-7] tricyclic ring skeleton of Calyciphylline alkaloids, specifically targeting Daphnilongeranin B. The study employs a concise photochemical [2+2] cycloaddition-Grob fragmentation sequence to synthesize the common tricyclic ring skeletons found in Calyciphylline A-type alkaloids, including daphnilongeranins, daphniyunnines, and daphniglaucins. The experiments utilize key steps such as Overman rearrangement, Mannich reaction, [2+2] photochemical cycloaddition, and Grob fragmentation. Reactants include (S)-(+)-carvone as the starting material, which is converted through a series of reactions involving CCl3CN, MOMCl, TBSOTf, and other reagents to construct the tricyclic core. The analyses used to confirm the structures and stereochemistry of the synthesized compounds include single crystal X-ray analysis and NMR spectroscopy, with detailed experimental procedures and compound characterization data provided in the supporting information.

Two-carbon-elongated HIV-1 protease inhibitors with a tertiary-alcohol- containing transition-state mimic

10.1021/jm070680h

The research focuses on the development of a new generation of HIV-1 protease inhibitors featuring a tertiary-alcohol-based transition-state mimic. The study involves the elongation of the core structure of existing inhibitors by two carbon atoms and variation of the P1′ group to enhance inhibitory potency. The main experiments include the synthesis of two-carbon-elongated analogues using (S)-2-hydroxy-3-phenylpropionic acid as a starting material, followed by a series of chemical reactions to introduce different P1′ substituents. The synthesized inhibitors were then biologically evaluated for their antiviral activities, with measurements of Ki and EC50 values. X-ray crystallography was also employed to determine the binding modes of the inhibitors with the HIV-1 protease. The analyses revealed that the new inhibitors exhibited improved enzyme inhibition activities and cellular anti-HIV activities, with some compounds showing high permeability and metabolic stability. Reactants used in the synthesis include (S)-2-hydroxy-3-phenylpropionic acid, various hydrazides, and protecting groups like TBSOTf, among others. The study also investigated the effects of different P1′ groups on the inhibitors' activities, leading to the identification of new terminal P1′ substituents that improved antiviral activity.

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