A stereoselective approach for the synthesis of alpha-sialosides.
A highly efficient synthesis of the human melanoma associated antigen GD(3) derivative has been described. A key feature of the synthetic approach was the use of sialyl donors that were protected with a C-5 trifluoroacetamide moiety. These sialyl donors gave high yields and excellent alpha-anomeric selectivities in direct glycosylations with a wide variety of glycosyl acceptors ranging from C-8 hydroxyls of sialic acids and C-3 hydroxyls of galactosides to reactive primary alcohols.
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Complex Carbohydrate Research Center, University of Georgia, 220 Riverbend Road, Athens, Georgia 30602, USA.
Demchenko
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AV
Boons
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GJ
D005697:Galactosides / Q000138:chemical synthesis* / Q000737:chemistry; D005732:Gangliosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D006801:Humans; D008968:Molecular Conformation; D019158:N-Acetylneuraminic Acid / Q000737:chemistry
D005697:Galactosides; D005732:Gangliosides; C049132:9-O-acetyl-GD3 ganglioside; D019158:N-Acetylneuraminic Acid