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Efficient deprotection of N<sup>G</sup>-tosylarginine with a thioanisole–trifluoromethanesulphonic acid system
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1980
Year
Bioorganic ChemistryEngineeringBiochemistryNatural SciencesO-to-c Rearrangement ProductsDiversity-oriented SynthesisGuanidino FunctionEfficient DeprotectionOrganic ChemistryHalogenationPharmaceutical ChemistryBiomolecular EngineeringChromatographyTosyl Group
The tosyl group attached at the guanidino function of arginine can be efficiently cleaved by a thioanisole–trifluoromethanesulphonic acid system, which can deprotect O-2,6-dichlorobenzyltyrosine without the formation of O-to-C rearrangement products; the NG-mesitylene-2-sulphonyl group was also cleaved by a thioanisole–trifluoroacetic acid system.