title: Practical synthesis of the 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucosides of Fmoc-serine and Fmoc-threonine and their benzyl esters.
abstract: Mercuric bromide-promoted glycosylation of Fmoc-Ser-OBn and Fmoc-Thr-OBn with 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-alpha-D-glucopyranosyl chloride in refluxing 1,2-dichloroethane gave the corresponding beta-glycosides in good yields (64 and 62%, respectively). Direct coupling of the commercially available Fmoc-Ser-OH and Fmoc-Thr-OH carboxylic acids under similar conditions gave the corresponding beta-glycosides, possessing free carboxyl groups, in moderate yields (50 and 40%, respectively).
authors.affiliation: Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Brazil.
authors.forename: Ivone
authors.initials: I
authors.lastname: Carvalho
authors.forename: Shona L
authors.initials: SL
authors.lastname: Scheuerl
authors.forename: K P
authors.initials: KP
authors.lastname: Ravindranathan Kartha
authors.forename: Robert A
authors.initials: RA
authors.lastname: Field
mesh_terms: D001554:Benzene / Q000737:chemistry*; D001965:Bromides / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D004952:Esters; D005025:Ethylene Dichlorides / Q000737:chemistry; D005960:Glucosides / Q000138:chemical synthesis*; D006031:Glycosylation; D008628:Mercury / Q000737:chemistry; D015394:Molecular Structure; D012694:Serine / Q000737:chemistry*; D013912:Threonine / Q000737:chemistry*
chemical_list: D001965:Bromides; D002264:Carboxylic Acids; D004952:Esters; D005025:Ethylene Dichlorides; D005960:Glucosides; D013912:Threonine; D012694:Serine; D008628:Mercury; D001554:Benzene