Trimethylsilyl trifluoromethanesulfonate

Structural formula
General
Surname	Trimethylsilyl trifluoromethanesulfonate
other names	TMSOTf; Trimethylsilyl triflate; Trimethylsilyl trifluoromethanesulfonate;
Molecular formula	C 4 H 9 F 3 O 3 SSi
Brief description	colorless to light yellow liquid
External identifiers / databases
EC number	248-565-4
ECHA InfoCard	100.044.136
PubChem	65367
Wikidata	Q15427958
properties
Molar mass	222.25 g mol −1
Physical state	liquid
density	1.228 g cm −3
boiling point	77 ° C (80 mmHg)
Refractive index	1.36
safety instructions
H and P phrases	H: 226-314
	P: 280-305 + 351 + 338-310
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Trimethylsilyl trifluoromethanesulfonate is an ester of trifluoromethanesulfonic acid ( triflate ), which has a trimethylsilyl group . Its reactivity is similar to that of trimethylsilyl chloride and it is used as a reagent in organic synthesis.

Usage examples

By means of a condensation catalyzed by trimethylsilyl triflate, seven benzylated procyanidin trimers can be obtained stereoselectively in very high yields (epicatechin- (4 β -8) -epicatechin- (4 β -8) -epicatechin- ( procyanidin C1 ), catechin- (4 α -8 ) -catechin (4 α -8) -catechin- ( procyanidin C2 ), epicatechin- (4 β -8) -epicatechin- (4 β -8) -catechin- and epicatechin- (4 β -8) -catechin- (4 α -8) -epicatechin trimers.Deprotection of (+) - catechin and (-) - epicatechin trimers leads to four natural procyanidin trimers in good yields.

In the total synthesis of Taxol according to Takashi Takahashi , TMSOTf is used for glycosylation.

literature

Encyclopedia of Reagents for Organic Synthesis , 1999-2013, John Wiley and Sons, Inc., entry for Trimethylsilyl Trifluoromethanesulfonate, accessed September 13, 2017 .

Individual evidence

↑ ^a ^b Entry trimethylsilyl trifluoromethanesulfonate at Carbolution Chemicals, accessed on September 2, 2017.
↑ ^a ^b ^c ^d data sheet trimethylsilyl trifluoromethanesulfonate from Sigma-Aldrich , accessed on September 2, 2017 ( PDF ).
↑ Akiko Saito, Akira Tanaka et al. a .: Efficient Stereoselective Synthesis of Proanthocyanidin Trimers with TMSOTf-Catalyzed Intermolecular Condensation. In: Synlett. 2004, p. 1069, doi : 10.1055 / s-2004-822905 .
↑ Takayuki Doi, Shinichiro Fuse et al. a .: A Formal Total Synthesis of Taxol Aided by an Automated Synthesizer. In: Chemistry - An Asian Journal. 1, 2006, p. 370, doi : 10.1002 / asia.200600156 .

[carbolution-1] Entry trimethylsilyl trifluoromethanesulfonate at Carbolution Chemicals, accessed on September 2, 2017.

[Aldrich-2] ta sheet trimethylsilyl trifluoromethanesulfonate from Sigma-Aldrich , accessed on September 2, 2017 ( PDF ).

[DOI10.1055/s-2004-822905-3] Akiko Saito, Akira Tanaka et al. a .: Efficient Stereoselective Synthesis of Proanthocyanidin Trimers with TMSOTf-Catalyzed Intermolecular Condensation. In: Synlett. 2004, p. 1069, doi : 10.1055 / s-2004-822905 .

[DOI10.1002/asia.200600156-4] Takayuki Doi, Shinichiro Fuse et al. a .: A Formal Total Synthesis of Taxol Aided by an Automated Synthesizer. In: Chemistry - An Asian Journal. 1, 2006, p. 370, doi : 10.1002 / asia.200600156 .