6338-63-2Relevant articles and documents
Thioacetate deprotection
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Sheet 1/2, (2008/06/13)
A method of thioacetate deprotection by providing a compound of the formula R1—S—CO—R2, and reacting the compound with a quaternary ammonium cyanide salt in the presence of a protic solvent in an inert atmosphere to convert the compound to a product of the formula R1—SH. R1 is an organic group in which the bonding to sulfur is through a saturated carbon, and R2 is an aliphatic group.
Aliphatic thioacetate deprotection using catalytic tetrabutylammonium cyanide
Holmes, Brian T.,Snow, Arthur W.
, p. 12339 - 12342 (2007/10/03)
A series of thiol-functionalized organic compounds were selected to analyze the scope and efficiency of a new thioacetate deprotection method using catalytic tetrabutylammonium cyanide (TBACN) to effect the transformation of a thioacetate group to a free thiol in the presence of a protic solvent. Particularly attractive are the mild reaction and workup conditions, reduced byproduct formation typically seen using literature methods and yields of greater than 80% for the free aliphatic thiols. This method is effective on aliphatic thiols with trityl, benzyl, p-halo-benzyl, phenethyl, phenoxyethyl, and cyclohexylethyl structural moieties, but it is not effective with thiophenols.