Medium heterocyclic rings from carbohydrate precursors

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Abstract
Chemical and physical evidence is presented to show that the structure of a dianhydride of D-ribose is di-β-D-ribofuranose 1,5′:1′,5-dianhydride. Partial acid hydrolysis of this dimer affords a ribobiose, which is shown to be 5-O-β-D-ribofuranosyl-D-ribose, since examination of the O-methyl derivative of this disaccharide yields 2,3,5-tri- and 2,3-di-O-methyl-D-ribose, and since quantitative measurements of the periodate consumption of the derived glycitol (4 moles of periodate per mole) are consistent with a structure corresponding to 5-O-β-D-ribofuranosyl-D-ribitol. In addition to confirming that both the 1 → 5′- and 1′ → 5- linkages have the β configuration, n.m.r. spectral data for the dianhydride tetraacetate leads to a conformational assignment for this derivative in chloroform at room temperature.Periodate oxidation of the dianhydride, followed by borohydride reduction and acetylation, yields a 2,4,7,9-tetraacetoxymethyl-1,3,6,8-tetraoxacyclodecane. The conformational properties of this compound are discussed.

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