A stereoselective alpha-fucosylation reaction using 1-hydroxy 2,3,4-tri-O-benzyl-L-fucose donor for the practical synthesis of selectin blocker.
A 1-hydroxy 2,3,4-tri-O-benzyl-L-fucose donor affords a high stereoselectivity of glycosylation in the presence of TMSOTf and is a very useful substrate for the preparation of an alpha-L-fucosyl dipeptide in a stereoselective manner. The donor will be a key component in the preparation of an attractively biological selectin blocker 1.
Kiyoi
T
T
Department of Chemistry, Pharmaceutical Laboratories, Kanebo Ltd., Osaka, Japan.
Kondo
H
H
D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry* / Q000494:pharmacology; D002240:Carbohydrate Sequence; D004151:Dipeptides / Q000737:chemistry*; D005643:Fucose / Q000031:analogs & derivatives* / Q000737:chemistry; D006031:Glycosylation; D008969:Molecular Sequence Data; D019087:Selectins / Q000378:metabolism*; D013237:Stereoisomerism
C116813:1-hydroxy-2,3,4-tri-O-benzylfucopyranose; C116820:2-hexadecylhexadecanoyl-(O-(1-O-fucopyranosyl))seryl-glutamic acid N-methylamide; D000894:Anti-Inflammatory Agents, Non-Steroidal; D004151:Dipeptides; D019087:Selectins; D005643:Fucose