The Journal of Organic Chemistry

The p-(methylsulfinyl) benzyl group: A trifluoroacetic acid (TFA)-stable carboxyl-protecting group readily convertible to a TFA-labile group

JM Samanen, E Brandeis

Index: Samanen, James M.; Brandeis, Ester Journal of Organic Chemistry, 1988 , vol. 53, # 3 p. 561 - 569

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Citation Number: 56

Abstract

The p-(methylsulfiiy1) benzyl or Msib ester is recommended as a selectively cleavable carboxyl-protecting group for peptide synthesis. Peptide or amino acid esters of p- (methylsulfiny1) benzyl alcohol, HO-Msib (2), or p-(methy1thio) benzyl alcohol, HO-Mtb (l), are readily prepared from the corresponding alcohols or alkyl halides. Msib esters may also be obtained from Mtb esters by oxidation with m-chloroperbenzoic acid. Msib esters are ...