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• W2024076783 endingPage "4178" @default.
• W2024076783 startingPage "4159" @default.
• W2024076783 abstract "The monosaccharide components of the O-specific polysaccharide 1 of the lipopolysaccharide of the enteropathogenic bacterium Shigella sonnei were synthesized as their methyl glycosides 2 and 3 in their natural anomeric form. The key intermediate to the diaminotrideoxygalactose derivative 2 was ethyl 3-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-d-glucopyranoside (9) that was converted to its ditosylate 10. Regioselective deoxygenation at C-6 followed by nucleophilic displacement of the secondary tosyloxy group by azide afforded the 4-azido thioglycoside 13. Methyl trifluoromethanesulfonate-assisted methanolysis of 13 gave the O-glycoside 14. Replacement of the phthalimido by an acetamido group followed by catalytic reduction of the azido group led to the diamino-trideoxygalactose derivative 2. The precursor to the l-altruronic acid derivative 3 was methyl α-l-glucopyranoside (19) that was routinely converted to the benzylidene-protected 2,3-anhydro-allopyranoside 22. Regioselective opening of the epoxide ring by NaN3 afforded the 2-azido derivative 23 that was benzylated at HO-3. Hydrolytic removal of the benzylidene group followed by TEMPO oxidation of C-6 and subsequent esterification with MeI gave the key l-azido-altruronic acid intermediate 29 that was transformed to the acetamidoaltruronic acid derivative 3. High resolution NMR data of the altruronic acid derivatives indicate that the conformation of their pyranose ring is crucially dependent on the substitution pattern: the 2-azido altruronic acid derivatives prefer the 4C1 conformation whereas the 2-acetamido congeners exist preferentially in the 1C4 conformation." @default.
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• W2024076783 date "1997-03-01" @default.
• W2024076783 modified "2023-10-16" @default.
• W2024076783 title "Synthesis of the monosaccharide units of the O-specific polysaccharide of Shigella sonnei" @default.
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• W2024076783 doi "https://doi.org/10.1016/s0040-4020(97)00145-2" @default.
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