A facile synthesis of α-d-galactopyranosyl-(1 → 1)-α-d-galactopyranoside and its analogues

Synthesis and Antigenic Evaluation of Oligosaccharide Mimics of Vi Antigen from Salmonella typhi

“…The other tetrasaccharide derivative 41 was built up starting from 28 in two tandem steps to install the azido group while maintaining the axial configuration of the C4 position at the non‐reducing end (Scheme ). First, triflation followed by treatment with sodium nitrite and imidazole in DMF gave 40 with inversed stereochemistry at the C4 position. Subsequently, triflation and azido substitution furnished tetrasaccharide 41 .…”

Improved Synthesis of 6-Azido-6-deoxy- and 6,6′-Diazido-dideoxy-α,α-trehaloses

“…1,2 We also reported the synthesis of a gluco-galacto analogue of trehalose for the same purpose. 3,4 Trehalosamines have been isolated from microorganisms and been synthesized and found to have antimicrobial activity, 5,6 and several groups of investigators have recently reported the syntheses of 6-amino-and 6,6′-diamino-α,α-trehalose. [7][8][9] In the present study, we describe a convenient synthesis of 6-azido-and 6,6′-diazido-α,α-trehalose compounds in which we have used the triflate derivatives of the partially trimethylsilylated-α,α-trehaloses, displacing the trifluoromethanesulfonate group by azide in the presence of a crown ether in N,N-dimethylformamide at room temperature.…”