Synthesis of sorbistin analogues

Synthesis of Oligosaccharides Related to a Biodynamic Saponin from Calamus Insignis as Their Propargyl Glycosides

“…Therefore, we opted for the H 2 SO 4 /silica-promoted reaction. The complete removal of the benzylidene acetal with 80 % AcOH at 80°C [22] followed by the selective protection of the primary hydroxy with the tert-butyldiphenylsilyl group afforded the disaccharide acceptor 8 in 84 % yield. The glycosylation of disaccharide acceptor 8 with the known glucosyl donor 9 [23] using NIS in the presence of H 2 SO 4 /silica afforded the protected trisaccharide 10 in 91 % yield.…”

Chemical synthesis of the pentasaccharide repeating unit of the O-specific polysaccharide from Escherichia coli O132 in the form of its 2-aminoethyl glycoside

“…First, the phthalimido group was removed using ethylenediamine [26] followed by acetylation with Ac 2 O in the presence of pyridine [27] to furnish the desired acetamido functionality. Next, the benzylidene group was hydrolyzed using 80% AcOH at 80 ºC [28]. Further, Zemplén de- O -acetylation using NaOMe in MeOH followed by hydrogenolysis in a ThalesNano continuous flow hydrogenation assembly using a 10% Pd-C cartridge [29].…”

Convergent synthesis of the hexasaccharide related to the repeating unit of the O-antigen from E. coli O120

“…The remaining primary hydroxyl group was further acetylated in the presence of Ac Further, the benzylidene ring of the trisaccharide 10 was hydrolyzed using 80% AcOH at 80 C (ref. 15) to form the diol 11 in 91% yield. Selective chloroacetylation of the primary hydroxyl group was achieved using chloroacetic anhydride and Et 3 N 16 at À5 C to form the desired trisaccharide acceptor 12 in 89% yield.…”