540533-95-7Relevant academic research and scientific papers
Side-chain-functionalized dipeptides derived from 6,5-fused bicyclic thiazolidinlactams
Tremmel, Peter,Brand, Joerg,Knapp, Volker,Geyer, Armin
, p. 878 - 884 (2007/10/03)
Condensation of D-arabinuronolactone (2) with L-cysteine methyl ester yields the bicyclic thiazolidinlactam 3 as a single diastereoisomer with the new bridgehead stereocenter in the (S) configuration. Regioselective activation of the a-hydroxy group leads to the triflate 4 without requiring protecting groups on the residual hydroxy groups. Subsequent azide exchange, reduction, and Boc protection, yields the epimeric dipeptide mimetics 6 and 7. Compound 3 forms the single acetonide 9, which permits the regioselective alkylation of the γ-hydroxy group of the bicyclic framework. Subsequent deprotection and exchange of the α-hydroxy functionality against a Boc-protected amino group (13) demonstrates the regioselective side-chain modification of bicyclic dipeptides. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
