✍ Scribed by Jens Andersch; Dieter Sicker; Horst Wilde
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Spiro[1,4-benzothiazine-2,2'-pyrans] Starting from Methyl β-D-arabino-2-Hexulopyranosonate. -Based on sugar (I), the cyclic hydroxamic acid (VI) and the lactams (VIII) and (IX) are prepared via the thiophenyl glycosides (V) and (VII). The spirobenzothiazinepyrans (VI), (VIII), and (IX) are the first examples of a novel class of heterocycles structurally related to bioactive natural products. The glycosides (V) and (VII) adopt a 5 C 2 conformation of the pyranoid ring whereas the benzothiazine system in (VI), (VIII), and (IX) forces a change into the 2 C 5 conformation.
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Synthesis of 5-Hydroxy-2-(β-D-ribofuranosyl)pyran-4-one from a Pyranulose Glycoside. -The title compound (VI) is synthesized from the pyranulose glycoside (I) by bromination, acetylation with Ac 2 O, and final deprotection with ammonia. -(KANAZAWA, SHIGEYUKI; MIZUNO,