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.

SYNTHESIS OF 4-DEOXY-L- (AND D-) HEXOSES FROM CHIRAL NON-CARBOHYDRATE BUILDING BLOCKS

GUARAGNA, ANNALISA
;
DE NISCO, MAURO;PALUMBO, GIOVANNI;PEDATELLA, SILVANA;FESTA, PASQUALE;CAPUTO, ROMUALDO
2004

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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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11588/7161
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