Di-tert-butylbis(trifluoromethanesulfonyloxy)silane

Base Information

• Chemical Name: Di-tert-butylbis(trifluoromethanesulfonyloxy)silane
• CAS No.: 85272-31-7
• Molecular Formula: C10H18F6O6S2Si
• Molecular Weight: 440.457
• Hs Code.: 29319090
• European Community (EC) Number: 680-172-7
• DSSTox Substance ID: DTXSID50337994
• Nikkaji Number: J364.545B
• Wikidata: Q72470111
• Mol file: 85272-31-7.mol

Synonyms:85272-31-7;di-tert-Butylsilyl bis(trifluoromethanesulfonate);Di-tert-butylbis(trifluoromethanesulfonyloxy)silane;Di-tert-butylsilanediyl bis(trifluoromethanesulfonate);[ditert-butyl(trifluoromethylsulfonyloxy)silyl] trifluoromethanesulfonate;DTBS ditriflate;Di-tert-butylsilyl ditriflate;Di-tert-butylsilylBis(trifluoromethanesulfonate);Di-t-butylsilybis(trifluoromethanesulfonate;Bis(trifluoromethanesulfonic acid)di-tert-butylsilanediyl ester;di-t-butylsilylbis(trifluoromethanesulfonate);di-t-butylsilyl bis(trifluoromethanesulfonate);Trifluoromethanesulfonic acid di-tert-butylsilylene ester;C10H18F6O6S2Si;SCHEMBL12936595;DTXSID50337994;MFCD00010581;AKOS015837779;CS-W009662;FS-4632;AC-32462;D3135;FT-0625367;D78536;S05900;Di-tert-butylbis(trifluoromethylsulfonyloxy)silane;A841277;di-tert-butylsilyl bis(trifluoromethane sulfonate);di-tert-butylsilyl bis(trifluoromethanesulphonate);Bis(tert-butyl)silyl bis(trifluoromethanesulphonate);Di-tert-butylsilyl bis(trifluoromethanesulfonate), 97%;[Di-tert-butyl(trifluoromethylsulfonyloxy)silyl] trifluoromethanesulfonate;Di-tert-butylsilyl bis(trifluoromethanesulfonate), purum, >=96.0% (GC);Methanesulfonic acid, trifluoro-, bis(1,1-dimethylethyl)silylene ester;Di(tert-butyl)([(trifluoromethyl)sulfonyl]oxy)silyl trifluoromethanesulfonate #;Di-tert-butylsilyl ditriflate DTBS ditriflate Trifluoromethanesulfonic acid di-tert-butylsilylene ester

Chemical Property of Di-tert-butylbis(trifluoromethanesulfonyloxy)silane

Chemical Property:

• Refractive Index: n20/D 1.398(lit.)
• Boiling Point: 275.6 °C at 760 mmHg
• Flash Point: 140.3 °C
• PSA: 103.50000
• Density: 1.389 g/cm³
• LogP: 5.92280
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: sol most common organic solvents.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 6
• Exact Mass: 440.02182614
• Heavy Atom Count: 25
• Complexity: 623

Purity/Quality:

99% ^*data from raw suppliers

Di-tert-butylsilyl Bis(trifluoromethanesulfonate) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C(C)(C)C)(OS(=O)(=O)C(F)(F)F)OS(=O)(=O)C(F)(F)F
• Physical properties: bp 73–75°C/0.35 mmHg; d 1.208 g cm?3.
• Uses: Di-t-butylsilyl bis(trifluoromethanesulfonate) is a reagent for the selective protection of polyhydroxy compounds. This reagent reacts with 1,2-, 1,3-, and 1,4-diols under mild conditions to give the corresponding dialkylsilylene derivatives in high yield (0–50°C, 79–96%). Deprotection is conveniently achieved by using aqueous hydrofluoric acid in acetonitrile (eq 1).Unlike di-t-butyldichlorosilane, this reagent reacts with hindered alcohols. Even pinacol reacts to give the silylene derivative (100°C, 24 h, 70%). Di-t-butylsilylene derivatives of 1,2-diols are more reactive than those of 1,3- and 1,4-diols and undergo rapid hydrolysis (5 min) in THF/H2O at pH 10, while the 1,3- and 1,4- derivatives are unaffected at pH 4–10 (22°C) for several hours. This protecting group is stable under the conditions of PDC oxidation of alcohols (CH2Cl2, 25?C, 27 h) and tosylation of alcohols (pyridine, 25°C, 27 h).The reagent has seen limited use for the protection of alcohols but has been used to protect nucleosides (eq 2).The procedure consists of sequential addition of the ditriflate and triethylamine to the nucleoside in DMF. The choice of solvent is critical. Protecting group reagent for 1,3-diols used recently in a synthesis of N-homoceramides. Also used for selective α-galactosylation in the synthesis of α-galactosyl ceramides.

Technology Process of Di-tert-butylbis(trifluoromethanesulfonyloxy)silane

There total 2 articles about Di-tert-butylbis(trifluoromethanesulfonyloxy)silane 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: 71.0%

trifluorormethanesulfonic acid (1493-13-6) + di-tert-butylchlorosilane (56310-18-0) → di-tert-butylsilyl bis(trifluoromethanesulfonate) (85272-31-7)

Guidance literature:

for 2h; Heating;

DOI:10.1016/S0040-4039(00)85735-4

Reference yield:

Di-tert-butyldichlorosilane (18395-90-9) → di-tert-butylsilyl bis(trifluoromethanesulfonate) (85272-31-7)

Guidance literature:

With silver trifluoromethanesulfonate;

Reference yield: 100.0%

(2S,3S)-2-[1,3]Dithian-2-yl-4-trityloxy-butane-1,3-diol (874117-56-3) + di-tert-butylsilyl bis(trifluoromethanesulfonate) (85272-31-7) → (4S,5S)-2,2-Di-tert-butyl-5-[1,3]dithian-2-yl-4-trityloxymethyl-[1,3,2]dioxasilinane (874117-66-5)

Guidance literature:

With pyridine; In dichloromethane; at -78 - -20 ℃;

DOI:10.1021/ol052335x

upstream raw materials:

Di-tert-butyldichlorosilane

trifluorormethanesulfonic acid

di-tert-butylchlorosilane

Downstream raw materials:

(4S,5R)-2,2-Di-tert-butyl-4,5-diphenyl-[1,3,2]dioxasilolane

(2S,3S)-2-((4S,5R)-4-Benzo[1,3]dioxol-5-yl-2,2-di-tert-butyl-[1,3,2]dioxasilinan-5-yl)-3-(1-ethoxy-ethoxy)-3-(3,4,5-trimethoxy-phenyl)-propionic acid methyl ester

(2R,3S,4S,5S,6E)-2,4,6-trimethyl-3,5-<dioxy>-1-phenylmethoxy-6-nonene

(4S,5R,6R)-4-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-6-isopropenyl-5-methyl-[1,3,2]dioxasilinane

Refernces

• 1、 Corey, E. J.,Hopkins, Paul B.. "DIISOPROPYLSILYL DITRIFLATE AND DI-tert-BUTYLSILYL DITRIFLATE: NEW REAGENTS FOR THE PROTECTION OF DIOLS". . p. 4871 - 4874. Retrieved 2007/10/02.