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|Title||Substituted 1, 2-thiazetidine 1, 1-dioxides. Synthesis of (RS)-and (S)-1, 2-thiazetidine-3-acetic acid 1, 1-dioxide and its reactions with amino acids and dipeptides|
(RS)-2-tert-Butyldimethylsilyl-1,2-thiazetidine-3-acetic acid 1,1-dioxide prepared from (RS)-S-benzyl-β-homocysteine was condensed via DCC/NHS with various L-amino acid esters or dipeptide esters yielding N-silylated β-sultam peptides. A β-sultam active ester was isolated as an intermediate. Desilylation with TBAF in THF yielded stable N-unsubstituted products, and deprotection of the benzyl esters was achieved by catalytic hydrogenation. (S)-S-Benzyl-β-homocysteine was obtained by fractional crystallization of the brucine salt of the racemate and transformed into benzyl (S)-1,2-thiazetidine-3-acetate, which was on the other hand synthesized by an enantiospecific route from ω-benzyl Boc-L-aspartate. Some β-sultam peptides were prepared from the (S)-enantiomer, and finally some β-sultam peptides containing D-Ala units were obtained.
|Published in||Monatshefte für Chemie/Chemical Monthly|
|Series||Volume: 135, Number: 8|
|Item link||Item Link|
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