Synthesis of 1,6-Anhydro-2-O-trifluoromethanesulphonyl-0-D-mannopyranose Derivatives and Their Conversion Into the Corresponding 1.6-Anhydro-2-azido-2-deoxy-β-D-glucopyranoses: A Convenient and Efficient Approach

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Abstract
Acid catalysed treatment of 1,6-anhydro-β-D-mannopyranose 1 with either benzaldehyde-, 4-methoxybenzaldehydl′- or acrolein dimethyl acetal afforded the corresponding dioxolane acetals 2–4. The C-4 hydroxyl function was subsequently protected by a variety of protective groups to give fully protected mannose derivatives 5±7.] Reductive opening of the endo isomers of the benzylidene, 4-me-thoxybenzylidene and prop-2-enylidene acetals in compounds 5±7 gave the corresponding axial ethers 8, 10 and 11. Oxidative opening of a mixture of isomers of the 4-methoxybenzylidene acetal in 6 resulted in the regioselective formation of axial 4-methoxybenzoyl esters 9. Triflation at the C-2 position of compounds 8±11, followed by treatment with lithium azide at room temperature yielded the corresponding 1,6-anhydro-2-azido-2-deoxy-3β-D-glucopyranose derivatives 16±19 in high yields.

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