SYNTHESIS OF A TETRAHYDROPYRANO[2,3-D]OXAZOLE ANALOG OF TREHAZOLIN

Tetrahydropyrano[2,3-d]oxazole 6 as an analogue of trehazolin was synt hesized from compound 3, which is a protected 1,3-bis(beta-D-glucopyra nosyl)thiourea. In contrast, compound 10, a protected 1,3-bis(alpha-D- glucopyranosyl)thiourea, and 15, a mixed species having one alpha-D-gl ucopyranosyl group and one beta-D-glucopyranosyl group, did not yield the corresponding pyranooxazolines as anticipated, giving instead, res pectively, a furo[2,3-d]oxazole 14 and a complex mixture of unidentifi ed products. (C) 1996 Elsevier Science Ltd.