Syntheses of neoglycolipids with hexitol spacers between the saccharidic and the lipidic parts.
Four neoglycolipids having 2-amino-2-deoxy-D-glucose or D-galactose moieties linked to the lipidic part by a glucitol or a mannitol spacer-arm have been synthesized. The key step of the synthetic strategy was the regiospecific or regioselective beta-glycosylation of partially protected glucitol or mannitol acceptors by either 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-alpha-D-mannopyranosyl azide or 2,3,4,6-tetra-O-benzoyl-alpha-D-galactopyranosyl trichloroacetimidate donors.
Lafont
D
D
Laboratoire de Chimie Organique II, Unité Mixte de Recherche CNRS 5622, Université Lyon 1, Chimie Phyisique Electronique de Lyon, Villeurbanne, France. lafont@univ-lyon1.fr
Gross
B
B
Kleinegesse
R
R
Dumoulin
F
F
Boullanger
P
P
D005690:Galactose / Q000737:chemistry; D005944:Glucosamine / Q000737:chemistry; D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D008353:Mannitol / Q000737:chemistry; D015394:Molecular Structure; D013012:Sorbitol / Q000737:chemistry
D006017:Glycolipids; D008353:Mannitol; D013012:Sorbitol; D005944:Glucosamine; D005690:Galactose