title: Synthesis of C-glycosyl compounds of N-acetylneuraminic acid from D-gluconolactone.
abstract: A general strategy towards the synthesis of C-glycosyl compounds of N-acetylneuraminic acid (Neu5Ac) has been developed and successfully applied to the synthesis of C-methyl and C-phenyl derivatives. The key strategic elements are (i) chain extension of a D-gluconolactone derivative as C(6)-precursor with an allyl Grignard reagent as C(3)-precursor having in 2 position the C-linked aglycon moiety, (ii) stereoselective C-4/C-5 erythro-diol formation, (iii) 6-exo-trig selective heterocyclization, and (iv) installment of the 5-acetylamino and C-1 carboxylate functionalities. The efficiency and potential versatility of this approach was exemplified in the synthesis of C-methyl derivative 1 as target molecule.
authors.affiliation: Fachbereich Chemie, Universität Konstanz, Fach M 725, D-78457 Konstanz, Germany.
authors.forename: Ahmed I
authors.initials: AI
authors.lastname: Khodair
authors.forename: Richard R
authors.initials: RR
authors.lastname: Schmidt
mesh_terms: D005942:Gluconates / Q000737:chemistry; D006027:Glycosides; D007783:Lactones; D009682:Magnetic Resonance Spectroscopy; D009005:Monosaccharides / Q000138:chemical synthesis*; D019158:N-Acetylneuraminic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D009942:Organometallic Compounds; D013237:Stereoisomerism
chemical_list: C438934:C-glycoside; D005942:Gluconates; D006027:Glycosides; D007783:Lactones; D009005:Monosaccharides; D009942:Organometallic Compounds; D019158:N-Acetylneuraminic Acid; C010730:beta-glucono-1,5-lactone