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

摘要

Tetrahydropyrano[2,3-d]oxazole 6 as an analogue of trehazolin was synthesized from compound 3, which is a protected 1,3-bis(beta-D-glucopyranosyl)thiourea. In contrast, compound 10, a protected 1,3-bis(alpha-D-glucopyranosyl)thiourea, and 15, a mixed species having one alpha-D-glucopyranosyl group and one beta-D-glucopyranosyl group, did not yield the corresponding pyranooxazolines as anticipated, giving instead, respectively, a furo[2,3-d]oxazole 14 and a complex mixture of unidentified products. (C) 1996 Elsevier Science Ltd. [References: 22]