765910-35-8

Upstream product

• 123-76-2 levulinic acid 
• 765910-34-7 thioethyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-p-methoxybenzyl-β-D-glucopyranoside 
• 765910-46-1 allyl 4-O-acetyl-6-O-benzyl-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-β-D-glucopyranoside 
• 765910-31-4 allyl 6-O-benzyl-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-β-D-glucopyranoside 
• 765910-45-0 allyl 4,6-O-benzylidene-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-β-D-glucopyranoside 
• 765910-32-5 allyl 4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside 

Relevant academic research and scientific papers

Multi-gram synthesis of a hyaluronic acid subunit and synthesis of fully protected oligomers

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

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.