150920-80-2Relevant academic research and scientific papers
Synthesis of allyl O-[sodium (α-D-glycero-D-talo-2-octulopyranosyl)onate]-2 → 6)-2-acetamido-2-deoxy-β-D-glucopyranoside, a core constituent of the lipopolysaccharide from Acinetobacter calcoaceticus NCTC 10305
Gass,Strobl,Loibner,Kosma,Zahringer
, p. 69 - 84 (1993)
Reaction of methyl 2,6-anhydro-2,3-dideoxy-D-manno-2-octenoate 1 with 3-chloroperoxybenzoic acid gave the 2,3-anhydro derivative 2, which was converted into the per-O-acetylated anomeric methyl glycosides of D-glycero-D-galacto-2-octulopyranosylonic acid in good yield. Subsequent inversion of the configuration at C-3 and deprotection afforded sodium (methyl β-D-glycero-D-talo-2-octulopyranosid)onate. Alternatively, 2 was transformed into methyl (α-D-glycero-D-talo-2-octulopyranosyl bromide)onate derivatives. Reaction with methanol or allyl 2-acetamido-2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-β -D-glycopyranoside, promoted by silver triflate, gave good yields of the corresponding orthoester derivatives. Me3Si triflate-catalyzed orthoester rearrangement and removal of the protecting groups afforded sodium O-(methyl α-D-glycero-D-talo-2-octulopyranosid)onate and the disaccharide, allyl O-[sodium (α-D-glycero-D-talo-2-octulopyranosyl)onate]-(2 → 6)-2-acetamido-2-deoxy-β-D-glucopyranoside in high yield. Reaction of methyl 2,6-anhydro-2,3-dideoxy-D-manno-2-octenoate 1 with 3-chloroperoxybenzoic acid gave the 2,3-anhydro derivative 2, which was converted into the per-O-acetylated anomeric methyl glycosides of D-glycero-D-galacto-2-octulopyranosylonic acid in good yield. Subsequent inversion of the configuration at C-3 and deprotection afforded sodium (methyl β-D-glycero-D-talo-2-octulopyranosid)onate. Alternatively, 2 was transformed into transformed into methyl (α-D-talo-2-octulopyranosyl bromide)onate derivatives. Reaction with methanol or allyl 2-acetamido-2-2-deoxy-3,4-O-(1,1,3, 3-tetraisopropyldisiloxan-1,3-diyl)-β-D-glycopyranoside, promoted by silver triflate, gave good yields of the corresponding orthoester derivatives. Me3Si triflate-catalyzed orthoester rearrangement and removal of the protecting groups afforded sodium O-(methyl α-D-glycero-D-talo-2-octulopyranosid)onate and the disaccharide, allyl O-[sodium (α-D-talo-2-octulopyranosyl)onate]- (2→6)-2-acetamido-2-deoxy-β-D-glucopyranoside in high yield.
Synthesis of neoglycoproteins containing D-glycero-D-talo-oct-2-ulopyranosylonic acid (Ko) ligands corresponding to core units from Burkholderia and Acinetobacter lipopolysaccharide
Wimmer, Norbert,Brade, Helmut,Kosma, Paul
, p. 549 - 560 (2007/10/03)
Glycal esters of Kdo derivatives were converted into 2,3-anhydro intermediates, which were transformed into D-glycero-D-talo-oct-2-ulopyranosylonic acid (Ko), as well as 3-O- and 4-O-p-nitrobenzoyl-Ko derivatives. The exo-allyl orthoester derivative, methyl {5,7,8-tri-O-acetyl-4-O-(4-nitrobenzoyl)-2,3-O-[(1-exo-allyloxy)-ethylide ne]-D-glycero-β-D-talo-oct-2-ulopyranos}onate, prepared from the 4-O-pNBz-protected Ko derivative, was elaborated into the α-Ko allyl ketoside, the reducing disaccharide α-Kdop-(2→4)-Ko and the disaccharide α-Kdop-(2→4)-Kop-(2→OAll). Conversely, methyl[4,5,7,8-tetra-O-acetyl-3-O-(4-nitrobenzoyl)-α-D-glycero-D-talo-2-o ctulopyranosyl bromide]onate [Carbohydr. Res., 244 (1993) 69-84], was coupled with a Kdo acceptor to give the disaccharide α-Kop-(2→4)-Kdop-(2→OAll) after orthoester rearrangement and deprotection. The allyl glycosides were treated with cysteamine and converted into neoglycoproteins. The ligands correspond to inner core units from Acinetobacter haemolyticus and Burkholderia cepacia lipopolysaccharides. (C) 2000 Elsevier Science Ltd.
