title: L-fucose from vitamin C with only acetonide protection.
abstract: Addition of human milk oligosaccharides (HMO) to baby foods may protect infants from disease. As many simple HMOs are fucosylated this is likely to increase the demand for L-fucose as a synthetic building block. Any chemical synthesis must be cheap to compete with a biotechnological process. Acetonide is the only protecting group we have used in this new synthesis of L-fucose from vitamin C in 27% overall yield (purification by recrystallization; no chromatography required in the entire sequence).
authors.affiliation: Chemistry Research Laboratory, Department of Chemistry, University of Oxford , Mansfield Road, Oxford, OX1 3TA, U.K.
authors.forename: Zilei
authors.initials: Z
authors.lastname: Liu
authors.forename: Akihide
authors.initials: A
authors.lastname: Yoshihara
authors.forename: Mark R
authors.initials: MR
authors.lastname: Wormald
authors.forename: Sarah F
authors.initials: SF
authors.lastname: Jenkinson
authors.forename: Vicky
authors.initials: V
authors.lastname: Gibson
authors.forename: Ken
authors.initials: K
authors.lastname: Izumori
authors.forename: George W J
authors.initials: GW
authors.lastname: Fleet
mesh_terms: D001205:Ascorbic Acid / Q000737:chemistry*; D005643:Fucose / Q000138:chemical synthesis / Q000737:chemistry*; D006801:Humans; D007223:Infant; D008895:Milk, Human / Q000737:chemistry*; D015394:Molecular Structure; D009844:Oligosaccharides / Q000737:chemistry*
chemical_list: D009844:Oligosaccharides; D005643:Fucose; D001205:Ascorbic Acid