We are pursuing an approach of asymmetricsynthesis of fluorinated analogues of biologically active compounds. The framework of chiral carbon atoms of the target molecule is built up around a chiral fluorinated synthon, of synthetic origin, in which an optically pure sulphinyl residue works as a chiral auxiliary agent. The transformation of the (2S,3R)-3-fluoro-1[(R)-(4-methylphenyl)sulphinyl]-5-hexen-2-ol (1), obtained starting from (R)-methyl 4-methylphenyl sulphoxide, ethyl fluoroacetate, and allyl bromide, into the 2,3-dideoxy-3-fluoro-D-erythro-pentose (2) and into the 3,4-dideoxy-3-fluoro-D-arabino-hexose (3) will be described. The synthesis of other monofluoro-pentoses and hexoses will be described and we will report also the preparation of some nitrogen-containing compounds.
Asymmetric synthesis of fluorocarbohydrates
BRAVO, PIERFRANCESCO;RESNATI, GIUSEPPE;
1989-01-01
Abstract
We are pursuing an approach of asymmetricsynthesis of fluorinated analogues of biologically active compounds. The framework of chiral carbon atoms of the target molecule is built up around a chiral fluorinated synthon, of synthetic origin, in which an optically pure sulphinyl residue works as a chiral auxiliary agent. The transformation of the (2S,3R)-3-fluoro-1[(R)-(4-methylphenyl)sulphinyl]-5-hexen-2-ol (1), obtained starting from (R)-methyl 4-methylphenyl sulphoxide, ethyl fluoroacetate, and allyl bromide, into the 2,3-dideoxy-3-fluoro-D-erythro-pentose (2) and into the 3,4-dideoxy-3-fluoro-D-arabino-hexose (3) will be described. The synthesis of other monofluoro-pentoses and hexoses will be described and we will report also the preparation of some nitrogen-containing compounds.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
