Direkt zum Inhalt
Merck

A new approach for the N- and S-galactosylation of 5-arylidene-2-thioxo-4-thiazolidinones.

Carbohydrate research (2011-11-18)
Ahmed I Khodair, Jean-Pierre Gesson
ZUSAMMENFASSUNG

N- and S-galactosylation was carried out via the reaction of 5-((Z)-arylidene)-2-thioxo-4-thiazolidinones with 2,3,4,6-tetra-O-acetyl-α-d-galactopyranosyl bromide under alkaline conditions or under silylation conditions. Deacetylation of the N-galactosylation products was performed with concentrated hydrochloric acid in methanol (3.5%) or sodium methoxide in methanol without cleavage of the 2-thioxo-4-thaizolidinone ring by means of acid hydrolysis. The anomers were separated by flash column chromatography, and their configurations were assigned by NMR spectroscopy. The deprotected nucleosides were screened against leukemia L-1210 and were found inactive.

MATERIALIEN
Produktnummer
Marke
Produktbeschreibung

Sigma-Aldrich
Acetobrom-α-D-Galaktose, ≥93% (TLC)