Di-tert-butylsilanediyl bis(trifluoromethanesulfonate)
Di-tert-butylsilanediyl bis(trifluoroMethanesulfonate) · BIS(TRIFLUOROMETHANESULFONATE) · DI-TERT-BUTYLBIS(TRIFLUOROMETHANESULFONYLOXY)SILANE · DI-T-BUTYLSILYLBIS(TRIFLUOROMETHANESULFONATE) · DI-TERT-BUTYLSILYL DITRIFLATE · Di-tert-butylsilylbis(trifluoromethanesul · DTBS DITRIFLATE · Di-T-Butylsilylbis
Identifikatoren & physikalische Daten
| CAS No. | 85272-31-7 |
|---|---|
| Summenformel | C10H18F6O6S2Si |
| Durchschnittliche Molmasse | 440,456 g/mol |
| Monoisotopische Masse | 440,02182615 g/mol |
| SMILES | CC(C)(C)[Si](OS(=O)(=O)C(F)(F)F)(OS(=O)(=O)C(F)(F)F)C(C)(C)C |
| InChIKey | HUHKPYLEVGCJTG-UHFFFAOYSA-N |
| PubChem CID | 545813 |
| EC No. | 680-172-7 |
| DTXSID | DTXSID50337994 |
Chemische & physikalische Eigenschaften
| Siedepunkt | 73-75 °C/0.35 mmHg (lit.) |
|---|---|
| Dichte | 1.352 g/mL at 25 °C (lit.) |
| Brechungsindex | n20/D 1.398(lit.) |
| Flammpunkt | 195 °F |
| Lagerbedingungen | Inert atmosphere,Room Temperature |
| Löslichkeit | sol most common organic solvents. |
| Aggregatzustand | Oil |
| Farbe | Clear Pale Yellow |
| Wichte | 1.358 |
| BRN | 3569211 |
| Stabilität | Moisture Sensitive |
| InChI | InChI=1S/C10H18F6O6S2Si/c1-7(2,3)25(8(4,5)6,21-23(17,18)9(11,12)13)22-24(19,20)10(14,15)16/h1-6H3 |
| InChIKey | HUHKPYLEVGCJTG-UHFFFAOYSA-N |
| SMILES | C(F)(F)(F)S(O[Si](C(C)(C)C)(C(C)(C)C)OS(C(F)(F)F)(=O)=O)(=O)=O |
| CAS Datenbank | 85272-31-7(CAS DataBase Reference) |
Sicherheit & Vorschriften
| F | 10-21 |
|---|---|
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | No |
| UN-Transportnummer | UN 3265 8/PG 2 |
| Zollcode | 29319090 |
| R-Sätze (R) | 34 |
| Gefahrensymbole | C |
| hazard_note | Corrosive |
| Sicherheitshinweise (S) | 26-36/37/39-45 |
| Gefahrenklasse | 8Skin Corr. 1B |
| Verpackungsgruppe | III |
| Lagerklasse | 8A - Combustible corrosive hazardous materials |
Anwendungen & Verwendung
Verwenden
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, 25C, 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.
Herstellung & Synthese
synthetische
by the treatment of di-t-butylchlorosilane with trifluoromethanesulfonic acid, followed by distillation (71% yield).