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Regioselective Benzylation of 2-Deoxy-2-Aminosugars Using Crown Ethers: Application to a Shortened Synthesis of Hyaluronic Acid Oligomers.
Advanced Synthesis & Catalysis 2014 July 8
The combination of benzyl bromide, sodium hydroxide and 15-crown-5 in tetrahydrofuran is shown to be an efficient method for installing benzyl groups at both the 4- and 6-positions regioselectively directly from peracetylated N-trichloroacetyl-protected glucosamine and galactosamine. Application of this benzylation strategy proved to significantly shorten the synthetic route to hyaluronic acid tetra- and hexamers.
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