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Regioselective Benzylation of 2‐Deoxy‐2‐aminosugars using Crown Ethers: Application to a Shortened Synthesis of Hyaluronic Acid Oligomers
Authors:Chinmoy Mukherjee  Lin Liu  Nicola L. B. Pohl
Abstract: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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Keywords:benzylation  carbohydrates  phase‐transfer catalysis  protecting groups  trichloroacetyl group
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