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(hydroxymethyl)trimethyl-silan; (trimethylsilyl)-methano; Methanol, (trimethylsilyl)-; Silane, (hydroxymethyl)trimethyl-; TRIMETHYLHYDROXYMETHYLSILANE; (TRIMETHYLSILYL)METHANOL
Boiling Point:
121ºC (754 torr)
Canonical SMILES:
1.Efficient kinetic resolution of (R,S)-1-trimethylsilylethanol via lipase-mediated enantioselective acylation in ionic liquids.
Lou WY1, Zong MH. Chirality. 2006 Nov;18(10):814-21.
Efficient enantioselective acylation of (R,S)-1-trimethylsilylethanol {(R,S)-1-TMSE} with vinyl acetate catalyzed by immobilized lipase from Candida antarctica B (i.e., Novozym 435) was successfully conducted in ionic liquids (ILs). A remarkable enhancement in the initial rate and the enantioselectivity of the acylation was observed by using ILs as the reaction media when compared to the organic solvents tested. Also, the activity, enantioselectivity, and thermostability of Novozym 435 increased with increasing hydrophobicity of ILs. Of the six ILs examined, the IL C4MIm.PF6 gave the fastest initial rate and the highest enantioselectivity, and was consequently chosen as the favorable medium for the reaction. The optimal molar ratio of vinyl acetate to (R,S)-1-TMSE, water activity, and reaction temperature range were 4:1, 0.75, and 40 -50 degrees C, respectively, under which the initial rate and the enantioselectivity (E value) were 27.6 mM/h and 149, respectively.
2.Enantioselective esterification of racemic naproxen by lipases in organic solvent.
Tsai SW1, Wei HJ. Enzyme Microb Technol. 1994 Apr;16(4):328-33.
Enantioselective esterification of naproxen, 2-(6-methoxy-2-naphthyl) propionic acid, was attempted by lipases in nearly anhydrous isooctane. The nature of the alcohol affects the reactivity and enantioselectivity of the lipase from Candida cylindracea. Alcohols containing a trimethylsilyl group are highly reactive and enantioselective to the S-isomer of the acid. An optimal temperature around 65 degrees C and an enzyme concentration less than 7 mg ml-1 were proposed to resolve the racemate, with trimethylsilyl methanol as nucleophile, from a consideration of the enantiomeric ratio, the ester formation, and the resistance of mass transfer for the substrate.
3.Effect of solvent on enantioselective esterification of naproxen by lipase with trimethylsilyl methanol.
Tsai SW1, Wei HJ. Biotechnol Bioeng. 1994 Jan 5;43(1):64-8.
Improvement of stereoselective resolution of racemic Naproxen, 2-(6-methoxy-2-naphthyl)propionic acid, was attempted with esterifcation reaction by Candida cylindracea lipase. By carefully selecting the organic medium, a 72-time enhancement of yield of the desired S-ester was achieved. The optimal reaction temperature was approximately 53 degrees C, and an alcohol concentration between 20 mM and 40 mM in an 80% (v/v) isooctane and 20% (v/v) toluene mixture was found. (c) 1994 John Wiley & Sons, Inc.
4.Surfactant enhancement of (S)-naproxen ester productivity from racemic naproxen by lipase in isooctane.
Tsai SW1, Lu CC, Chang CS. Biotechnol Bioeng. 1996 Jul 20;51(2):148-56.
In the enantioselective esterification of racemic Naproxen with trimethylsilyl methanol in isooctane by Candida cylindracea lipase, improvements in (S)-naproxen ester productivity and enzyme selectivity were demonstrated by adding bis(2-ethylhexyl) sodium sulfosuccinate (AOT) as the best surfactant. The effect of water content on the enhancement of enzyme activity was elucidated from the reduced adsorption of surfactant molecules on the lipase. A competitive inhibition by the alcohol and a noncompetitive inhibition by the surfactant to the enzyme were found from the kinetic analysis. By using a two-phase extraction, a complete separation of the surfactant from the organic solution was obtained.
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