title: Multi gram-scale synthesis of galactothionolactam and its transformation into a galactonoamidine.
abstract: We recently proposed to conduct selective glycosylation reactions after in situ activation of a glycosyl donor promoted by a transition metal complex immobilized in a macromolecular matrix. In order to develop this catalytic entity, a feasible multi gram-scale synthesis for 2,3,4,6-tetra-O-benzyl-d-galactothionolactam, its transformation into galactonoamidines with aromatic aglycon, and subsequent debenzylation conditions were developed. The potential for epimerization reactions at C-2 of the glycosidic ring during the transformations from the 2,3,4,6-tetra-O-benzyl-d-galactonolactam into the N-benzyl-2,3,4,6-tetra-O-benzyl-d-galactonoamidines via the 2,3,4,6-tetra-O-benzyl-d-galactothionolactam are discussed and additionally characterized by using density functional theory calculations.
authors.affiliation: Auburn University, Department of Chemistry and Biochemistry, 179 Chemistry Building, Auburn, AL 36849, USA.
authors.forename: Rami
authors.initials: R
authors.lastname: Kanso
authors.forename: Susanne
authors.initials: S
authors.lastname: Striegler
mesh_terms: D000578:Amidines / Q000138:chemical synthesis*; D001593:Benzyl Compounds / Q000737:chemistry; D002384:Catalysis; D004355:Drug Stability; D005690:Galactose / Q000737:chemistry; D006031:Glycosylation; D007769:Lactams / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000578:Amidines; D001593:Benzyl Compounds; D007769:Lactams; D005690:Galactose