title: Glycosyl alkoxythioimidates as complementary building blocks for chemical glycosylation.
abstract: It is reported that S-glycosyl O-methyl phenylcarbamothioates (SNea carbamothioates) have a fully orthogonal character in comparison to S-benzoxazolyl (SBox) glycosides. This complete orthogonality was revealed by performing competitive glycosylation experiments in the presence of various promoters. The results obtained indicate that SNea carbamothioates have a very similar reactivity profile to that of glycosyl thiocyanates, yet are significantly more stable and tolerate selected protecting group manipulations. These features make the SNea carbamothioates new promising building blocks for further utilization in oligosaccharide synthesis.
authors.affiliation: Department of Chemistry and Biochemistry, University of Missouri-St. Louis, One University Boulevard, St. Louis, Missouri 63121, USA.
authors.forename: Sneha C
authors.initials: SC
authors.lastname: Ranade
authors.forename: Sophon
authors.initials: S
authors.lastname: Kaeothip
authors.forename: Alexei V
authors.initials: AV
authors.lastname: Demchenko
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D006031:Glycosylation; D007096:Imidoesters / Q000737:chemistry*; D015394:Molecular Structure; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D000438:Alcohols; D007096:Imidoesters; D013438:Sulfhydryl Compounds; C059688:alkoxyl radical