765910-34-7Relevant academic research and scientific papers
Multi-gram synthesis of a hyaluronic acid subunit and synthesis of fully protected oligomers
Virlouvet, Mickael,Gartner, Michael,Koroniak, Katarzyna,Sleeman, Jonathan P.,Braese, Stefan
supporting information; experimental part, p. 2657 - 2662 (2011/01/05)
Fully protected tetra-, hexa- and octasaccharides of hyaluronic acid were synthesized on a scale of several 100 mg up to gram quantities using allyl (methyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-β-D-glucopyranosyluronate)- (1→3)-4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-β-D- glucopyranoside as a key building block. This disaccharide was subjected to deprotection, then glycosylation via the trichloroacetimidate method was employed to achieve the formation of the oligosaccharides.
Toward the modular synthesis of glycosaminoglycans: Synthesis of hyaluronic acid disaccharide building blocks using a periodic acid oxidation
Palmacci, Emma R.,Seeberger, Peter H.
, p. 7755 - 7766 (2007/10/03)
The synthesis of two differentially protected GluNAc-β(1→4)-GluA and GluA-β(1→3)-GluNAc disaccharide modules for the solid-phase assembly of hyaluronic acid are described. A periodic acid/chromium trioxide oxidation was the key transformation to facilitate access to the glucuronic acid moiety from glucose and should find wide application in the oxidation of primary alcohols.
