Synthesis of 4-deoxy-L-(and D-)hexoses from chiral noncarbohydrate building blocks |
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Authors: | Caputo Romualdo De Nisco Mauro Festa Pasquale Guaragna Annalisa Palumbo Giovanni Pedatella Silvana |
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Affiliation: | Dipartimento di Chimica Organica e Biochimica, Università di Napoli Federico II, Via Cynthia, 4 80126 Naples, Italy. |
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Abstract: | 4-Deoxy-l-hexoses were synthesized starting from our previously reported reagent 1 and (R)-benzyl glycidyl ether, which led in few steps to a substituted dihydropyran 6. The stereocontrolled hydroxylation of the latter afforded the corresponding 4-deoxy-l-hexoses 7a, 9, and 11. The same procedure, starting from (S)-benzyl glycidyl ether, enabled the preparation of their d-series enantiomers. |
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