Synthesis of a di-, tri-, and tetra-saccharide unit of the group B streptococcal common antigen

Abstract

Condensation of methyl 2,3- O-isopropylidene-α- l-rhamnopyranoside with methyl 3,4,6-tri- O-acetyl-2-deoxy-2-phthalimido-1-thio-β- d-glucopyranoside activated by nitrosyl tetrafluoroborate gave an excellent yield of the protected disaccharide 9, which was transformed into glycosyl acceptor 11. Methyl 2,3,4,6-tetra- O-acetyl-1-thio-β- d-galactopyranoside, obtained from d-galactose pentaacetate and methyl trimethylsilyl sulfide, under catalysis by boron trifluoride etherate, was converted into glycosyl donor 25, which was condensed with 11 under halide-ion catalysis to give the trisaccharide derivative 26. Rhamnosylation with 28 of 27, obtained by selective deprotection of 26, gave the protected tetrasaccharide 29. Deprotection of 10, 26, and 29 gave di- ( 2), tri- ( 3) and tetra-saccharide ( 4) methyl glycosides which form part of the group-specific polysaccharide antigen of Group B Streptococci.