Synthesis of hyaluronic acid oligosaccharides and exploration of a fluorous-assisted approach

• We describe the synthesis of hyaluronic acid oligosaccharides.
• Glucuronic acid units were employed in the glycosylation reactions.
• A three-step deprotection sequence afforded tri- and tetrasaccharide fragments.
• The use of a fluorous tag facilitated the purification of intermediates.

The synthesis of hyaluronic acid oligomers (tri- and tetrasaccharide) is described. We have followed a pre-glycosylation oxidation strategy. Glucuronic acid units were directly employed in coupling reactions with suitably protected glucosamine derivatives. In order to simplify the purification of synthetic intermediates, a fluorous-assisted strategy has been also explored. Using this approach, a hyaluronic acid trisaccharide was prepared.

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