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Gewählte Publikation:

Gass, J; Strobl, M; Loibner, A; Kosma, P; Zähringer, U.
(1993): Synthesis of allyl O-[sodium(alpha-D-glycero-D-talo-2- octulopyranosyl)onate]-(2-->6)-2-acetamido-2-deoxy-beta-D-glucopyranosi de, a core constituent of the lipopolysaccharide from Acinetobacter calcoaceticus NCTC 10305.
Carbohydr Res. 1993; 244(1):69-84

Abstract:
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 beta-D-glycero-D-talo-2-octulopyranosid)onate. Alternatively, 2 was transformed into methyl (alpha-D-glycero-D-talo-2-oc-tulopyranosyl bromide)onate derivatives. Reaction with methanol or allyl 2-acetamido-2-deoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-beta-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 alpha-D-glycero-D-talo-2-octulopyranosid)onate and the disacchanide, allyl O-[sodium (alpha-D-glycero-D-talo-2-octulopyranosyl)-onate]-(2 --> 6)-2-acetamido-2-deoxy-beta-D-glucopyranoside in high yield.
Autor/innen der BOKU Wien:
Kosma Paul
Loibner Andreas Paul
BOKU Gendermonitor:

Find related publications in this database (using NML MeSH Indexing)
Acinetobacter calcoaceticus - chemistry
Carbohydrate Conformation - chemistry
Carbohydrate Sequence - chemistry
Disaccharides - chemical synthesis
Indicators and Reagents - chemical synthesis
Lipopolysaccharides - chemistry
Magnetic Resonance Spectroscopy - chemistry
Molecular Sequence Data - chemistry
Optical Rotation - chemistry



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