A simple synthesis of 8-(methoxycarbonyl)octyl 3,6-di- O-(α- d-mannopyranosyl)-α- d-mannopyranoside and derivatives and their use in the preparation of neoglycoconjugates

8-(Methoxycarbonyl)octyl 3,6-di- O-(α- d-mannopyranosyl)-α- 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 prepar...

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Bibliographic Details
Published in:Carbohydrate research 1999-01, Vol.315 (1), p.148-158
Main Authors: Becker, Bernd, Furneaux, Richard H, Reck, Folkert, Zubkov, Oleg A
Format: Article
Language:English
Subjects:
Carbohydrate Sequence
Disaccharides - chemical synthesis
Glycoconjugates - chemical synthesis
Glycolipid
glycolipids
Mannosides - chemical synthesis
Mannotrioside
Molecular Sequence Data
Neoglycoconjugates
oligosaccharides
Synthesis
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Summary:8-(Methoxycarbonyl)octyl 3,6-di- O-(α- d-mannopyranosyl)-α- 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.
ISSN:0008-6215
1873-426X
DOI:10.1016/S0008-6215(98)00330-9