Total synthesis of hexuronic acids.
Six stereoisomeric hexuronic acids (tert-butyl esters of methyl pyranosides) having the altro, manno, gluco, gulo, galacto, and talo configurations were obtained from cis,trans-tert-butyl 2-methoxy-5,6-dihydro-2H-pyran-6-carboxylate (5). The synthesis involved the following successive steps: epoxidation of the double bond in 5, opening of the epoxides with dimethylamine, Cope degradation of the dimethyl-amino derivatives, and hydroxylation of the double bond in the tert-butyl hex-3-enuronates. All compounds were obtained as pure diastereoisomers in racemic form.
D006603:Hexuronic Acids / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014574:Uronic Acids / Q000138:chemical synthesis*
D006603:Hexuronic Acids; D014574:Uronic Acids