A simple synthesis of 8-(methoxycarbonyl)octyl 3,6-di-O-(alpha-D-mannopyranosyl)-alpha-D-mannopyranoside and derivatives and their use in the preparation of neoglycoconjugates.
8-(Methoxycarbonyl)octyl 3,6-di-O-(alpha-D-mannopyranosyl)-alpha-D-mannopyranoside (10) was synthesized in 54% yield by regioselective diglycosylation of unprotected mannoside 4, employing the trichloroacetimidate donor 1, followed by debenzoylation. Derivatives of compounds 4 and 10 were used to prepare conjugates containing fluorochromes for the study of carbohydrate-lectin interactions, as well as conjugates with phospholipids for the preparation of liposomes.
Becker
B
B
Industrial Research Ltd, Lower Hutt, New Zealand.
Furneaux
R H
RH
Reck
F
F
Zubkov
O A
OA
D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis*; D006001:Glycoconjugates / Q000138:chemical synthesis*; D008362:Mannosides / Q000138:chemical synthesis*; D008969:Molecular Sequence Data
C120598:8-(methoxycarbonyl)octyl 3,6-di-O-(mannopyranosyl)-mannopyranoside; D004187:Disaccharides; D006001:Glycoconjugates; D008362:Mannosides