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. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 69:21(2004), pp. 7033-7037. [10.1021/jo0493774]
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
