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Rapid Access to 1,6-Anhydro-β-l-hexopyranose Derivatives via Domino Reaction: Synthesis of l-Allose and l-Glucose

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journal contribution
posted on 2008-07-18, 00:00 authored by Daniele D’Alonzo, Annalisa Guaragna, Carmela Napolitano, Giovanni Palumbo
An expeditious and efficient synthesis of 1,6-anhydro-β-l-hexopyranosyl derivatives 3 as valuable building blocks for the preparation of l-sugars is herein reported. This route relies upon the use of a domino reaction involving five synthetic steps from the 5,6-dihydro-1,4-dithiin 4. As 1,6-anhydro derivatives 3 are obtained, dithioethylene bridge removal and double-bond dihydroxylation give access to protected l-allose and l-glucose in stereoselective fashion and high yields.