Substituted 1,2-Thiazetidine 1,1-Dioxides. Synthesis of (<Emphasis Type="Italic">RS</Emphasis>)- and (<Emphasis Type="Italic">S</Emphasis>)-1,2-Thiazetidine-3-acetic Acid 1,1-Dioxide and its Reactions with Amino Acids and Dipeptides |
| |
Authors: | Till?R?hrich Bassam?Abu Thaher Nico?Manicone Email author" target="_blank">Hans-Hartwig?OttoEmail author |
| |
Institution: | (1) Department of Pharmaceutical/Medicinal Chemistry (PMC), Institute of Pharmacy, Ernst-Moritz-Arndt-University, DE-17487 Greifswald, Germany |
| |
Abstract: | Summary. (RS)-2-tert-Butyldimethylsilyl-1,2-thiazetidine-3-acetic acid 1,1-dioxide prepared from (RS)-S-benzyl--homocysteine was condensed via DCC/NHS with various L-amino acid esters or dipeptide esters yielding N-silylated -sultam peptides. A -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--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 -benzyl Boc-L-aspartate. Some -sultam peptides were prepared from the (S)-enantiomer, and finally some -sultam peptides containing D-Ala units were obtained. |
| |
Keywords: | -Sultam, -Sultam Peptide," target="_blank">, 1,2-Thiazetidine 1,1-Dioxide, -Sultam, -Sultam Peptide, |
本文献已被 SpringerLink 等数据库收录! |
|