Abstract
Abstract Per-O-acetyl-β--glycopyranosylisothiocyanates (3 and 4) were condensed with 2-chloroethylamine hydrochloride to afford N,N'-bis(per-O-acetyl–β--glycopyranosyl)-N-(2-thiazolin-2-yl)thioureas (5 and 6) through the glycosylaminoheterocycles (7 and 8) as intermediates. Compounds 7 and 8 were converted into N-(2-thiazolin-2-yl)urea or thioureas (9–11) by reaction with iso(thio)cyanates. Compounds 5, 6 and 9–11 show a strong chelated structure due to an intramolecular hydrogen bond, which anchors the E,Z conformation in solution.
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