title: Preparation of 2-amino-2-C-glycosyl-acetonitriles from C-glycosyl aldehydes by Strecker reaction.
abstract: Synthesis of new 2-amino-2-C-D-glycosyl-acetonitriles in a Strecker reaction from various C-glycosyl aldehydes, chiral amines, and HCN was carried out. While aminonitriles from glycal and 2-deoxy-β-D-glycosyl aldehydes were prepared in satisfactory yields, lower yields were obtained with C-glycosyl aldehydes. Strecker reaction with the benzyl-protected 1-C-formyl-D-galactal and S- or R-1-phenylethylamine (S-PEA or R-PEA) yielded predominantly the R-configured C-glycosyl aminoacetonitrile. The direction of the nucleophilic addition appears to be governed by the configuration of the anomeric carbon with β-linked sugars. Since the stereochemistry of the transition state is unknown according to the configuration of the major product a Felkin-Ahn selectivity can be mainly presumed.
authors.affiliation: Institute of Biomolecular Chemistry, Chemical Research Center, Hungarian Academy of Sciences, PO Box 17, 1525 Budapest, Hungary.
authors.forename: Szabolcs
authors.initials: S
authors.lastname: Sipos
authors.forename: István
authors.initials: I
authors.lastname: Jablonkai
authors.forename: Orsolya
authors.initials: O
authors.lastname: Egyed
authors.forename: Mátyás
authors.initials: M
authors.lastname: Czugler
mesh_terms: D000097:Acetonitriles / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000097:Acetonitriles; D000447:Aldehydes