Portal de Periódicos da CAPES

Syntheses of 4- and/or 4′-Phosphate Derivatives of Methyl 3- O - l - Glycero -α- d - manno -heptopyranosyl- l - glycero α- d - manno -heptopyranoside and Their 2-(4-Trifluoro-acetamidophenyl)ethyl Glycoside Analogues.

1995; Taylor & Francis; Volume: 14; Issue: 3 Linguagem: Inglês

10.1080/07328309508002073

1532-2327

Kerstin Ekelöf, Stefan Oscarson,

Legume Nitrogen Fixing Symbiosis

Abstract Syntheses are described of the three disaccharides: methyl 3-O-L-glycero-α-D-manno-heptopyranosyl-L-glycero-α-D-manno-heptopyranoside 4-phosphate, methyl 3-O-(L-glycero-α-D-manno-heptopyranosyl 4-phosphate)-L-glycero-α-D-manno-heptopyranoside, and methyl 3-O-(L-glycero-α-D-manno-heptopyranosyl 4-phosphate)-L-glycero-α-D-manno-heptopyranoside 4-phosphate together with their 2-(4-trifluoroacetamidophenyl)ethyl glycoside analogues. These correspond to phosphorylated structures found in the inner core region of lipopolysaccharides from Salmonella. The known derivative methyl 6,7-di-O-acetyl-2,3,4-tri-O-benzyl-L-glycero-α-D-manno-heptopyranoside was used as a common heptose precursor. Phosphorylation on suitably protected disaccharide derivatives was performed by treatment with phosphorus triimidazolate in dichloromethane followed by the addition of benzyl alcohol and in situ oxidation with m-chloroperbenzoic acid to give the dibenzyltriester phosphate derivatives, which after deprotection gave the target compounds.