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Peer Reviewed Journal
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Ekeloef, Kerstin,Oscarson, Stefan;
1995
Syntheses of 4- and/or 4'-phosphate derivatives of methyl 3-O-L-glycero-a-D-manno-heptopyranosyl-L-glycero-a-D-manno-heptopyranoside and their 2-(4-trifluoroacetamidophenyl)ethyl glycoside analogs
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14
3
299
315
Syntheses are described of the three disaccharides: Me 3-O-L-glycero-a-D-manno-heptopyranosyl-L-glycero-a-D-manno-heptopyranoside 4-phosphate, Me 3-O-(L-glycero-a-D-manno-heptopyranosyl 4-phosphate)-L-glycero-a-D-manno-heptopyranoside, and Me 3-O-(L-glycero-a-D-manno-heptopyranosyl 4-phosphate)-L-glycero-a-D-manno-heptopyranoside 4-phosphate together with their 2-(4-trifluoroacetamidophenyl)ethyl glycoside analogs. These correspond to phosphorylated structures found in the inner core region of lipopolysaccharides from Salmonella. The known deriv. Me 6,7-di-O-acetyl-2,3,4-tri-O-benzyl-L-glycero-a-D-manno-heptopyranoside was used as a common heptose precursor. Phosphorylation on suitably protected disaccharide derivs. was performed by treatment with phosphorus triimidazolate in dichloromethane followed by the addn. of benzyl alc. and in situ oxidn. with m-chloroperbenzoic acid to give the dibenzyltriester phosphate derivs., which after deprotection gave the target compds., e.g. I (R = Me, CH2CH2PhNHCOCF3). [on SciFinder (R)]
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