THE PRODUCTS OF THE PREVOST REACTION ON D-GLUCAL TRIACETATE

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Abstract
The compound reported by Stanek and Schwarz (Collection Czechoslov. Chem. Communs. 20, 42 (1955)) to be 1-O-benzoyl-2-iodo-2-deoxy-α-D-glucopyranose triacetate is actually an approximately equimolar mixture of 1-O-benzoyl-2-iodo-2-deoxy-β-D-glucopyranose triacetate and the stereoisomer with the α-D-manno configuration. Methanolysis of these compounds yielded methyl 2-iodo-2-deoxy-β-D-glucopyranoside and methyl 2-iodo-2-deoxy-α-D-manno-pyranoside, respectively. Hydrogenolysis of the latter iodoglycosides using a palladium catalyst gave near-quantitative yields of the corresponding methyl 2-deoxy-D-glucopyranosides. Several other properties of the iodides are reported.