Synthesis of cerebroside, lactosyl ceramide, and ganglioside GM3 analogs containing beta-thioglycosidically linked ceramide.
Coupling of the sodium salt of 2,3,4,6-tetra-O-acetyl-1-thio-beta-D-glucopyranose, -beta-D-galactopyranose, O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-(1----4)-2,3,6-tri-O- acetyl- 1-thio-beta-D-glucopyranose, or O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D-galacto -2- nonulopyranosylonate)-(2----3)-O-(2,3-di-O-acetyl-6-O-bezoyl -beta-D- galactopyranosyl)-(1----4)-3-O-acetyl-2,6-di-O-benzoyl-1-thio-beta-D- glucopyranose, which were prepared from the corresponding 1-S-acetates, 1, 3, 6, and 9, with (2S,3R,4E)-2-azido-3-O-benzoyl-1-O-(p-tolylsulfonyl)-4-oc tadecene-1,3-diol (12) derived by tosylation of 11, gave the corresponding beta-thioglycosides 13, 17, 21, and 25, respectively in good yield. The beta-thioglycosides obtained were converted, via selective reduction of the azide group, condensation with octadecanoic acid, and removal of the protecting groups, into the title compounds.
Hasegawa
A
A
Department of Applied Bioorganic Chemistry, Gifu University, Japan.
Morita
M
M
Kojima
Y
Y
Ishida
H
H
Kiso
M
M
D002240:Carbohydrate Sequence; D002554:Cerebrosides / Q000138:chemical synthesis / Q000737:chemistry; D005679:G(M3) Ganglioside / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry; D007790:Lactosylceramides / Q000138:chemical synthesis / Q000737:chemistry; D008969:Molecular Sequence Data; D015394:Molecular Structure; D013865:Thioglycosides / Q000138:chemical synthesis* / Q000737:chemistry
D002554:Cerebrosides; D005679:G(M3) Ganglioside; D006017:Glycolipids; D007790:Lactosylceramides; D013865:Thioglycosides