title: De novo synthesis of uronic acid building blocks for assembly of heparin oligosaccharides.
abstract: An efficient de novo synthesis of uronic acid building blocks is described. The synthetic strategy relies on the stereoselective elongation of thioacetal protected dialdehydes 12 a and 17. The dialdehydes are prepared from D-xylose, a cheap and commercially available source. A highly stereoselective MgBr(2)OEt(2)-mediated Mukaiyama aldol addition to C4-aldehyde 12 a is performed to obtain D-glucuronic acid building block 16, whereas L-iduronic acid building block 22 is prepared by MgBr(2)OEt(2)-mediated cyanation of C5-aldehyde 17. Synthesis of a heparin disaccharide demonstrates the utility of the de novo strategy for the assembly of glycosaminoglycan oligosaccharides.
authors: Laboratory for Organic Chemistry, Swiss Federal Institute of Technology ETH Zürich, Wolfgang-Pauli-Strasse 10, HCI F312, 8093 Zürich, Switzerland.
authors: Alexander
authors: A
authors: Adibekian
authors: Pascal
authors: P
authors: Bindschädler
authors: Mattie S M
authors: MS
authors: Timmer
authors: Christian
authors: C
authors: Noti
authors: Nina
authors: N
authors: Schützenmeister
authors: Peter H
authors: PH
authors: Seeberger
mesh_terms: D018360:Crystallography, X-Ray; D006493:Heparin / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014574:Uronic Acids / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D009844:Oligosaccharides; D014574:Uronic Acids; D006493:Heparin