ABSTRACT
Thioglycosides, in which the anomeric oxygen is replaced by sulfur, receive considerable attention due to altered stability to chemical and enzymatic hydrolysis while their solution conformation and biological activities are comparable to native counterparts.1 Consequently, much effort has been devoted in the past two decades to the synthesis of thioglycosides, including thiosaccharides and S-glycoconjugates, in
Experimental ............................................................................................................98 General Methods .................................................................................................98 Synthesis of α-glycosyl thiols: General Procedure .............................................99 2,3,4-Tri-O-benzyl-1-thio-α-d-galactopyranose (5) ......................................... 100 2,3,4-Tri-O-benzyl-1-thio-α-d-glucopyranose (6) ............................................ 100 2,3-Di-O-allyl-4-O-benzyl-1-thio-α-d-glucopyranose (7) ................................ 100 2,3-Di-O-allyl-4-O-benzyl-1-thio-α-d-galactopyranose (8) ............................. 101
Acknowledgments .................................................................................................. 101 References .............................................................................................................. 105
order to provide valuable compounds for biological studies.2 For instance, carbohydrate epitopes of conjugate vaccines have been modied to contain S-linked residues and the resulting S-linked immunogens generated an antigen-specic immune response that exceeds the response to the native oligosaccharides.3
