Synthesis of the saccharomicin fucose-aglycon conjugate and determination of absolute configuration.
[reaction: see text] Schmidt glycosylation of the appropriately protected 3,4-dihydroxycinnamate methyl ester with 2,3,4-triacetoxyfucopyranosyltrichloroacetimidate gives aryl glycoside in high yield and diastereoselectivity. 2-Sulfation of fucose, installation of taurine, and global deprotection of the remaining protecting groups affords the fucose-aglycon conjugate of saccharomicin. This synthesis which arises from L-fucose also establishes the absolute configuration of the reducing terminus of the saccharomicin oligosaccharide.
Pletcher
Joseph M
JM
Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
McDonald
Frank E
FE
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002236:Carbohydrate Conformation; D005643:Fucose / Q000737:chemistry*; D006031:Glycosylation; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D009844:Oligosaccharides; D005643:Fucose