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Methyl 4-O-benzyl-2,3-anhydro-β-d-lyxopyranoside, an intermediate for the preparation of methyl β-d-xylopyranoside derivatives modified at C-2, was obtained in five steps in 58% yield. The synthetic sequence starts from methyl β-d-xylopyranoside through two main steps involving regioselective enzymatic acetylation and deacetylation catalyzed by lipase PS.
Four modified substrates for acetylxylan esterases, 2-deoxy, 3-deoxy, 2-deoxy-2-fluoro, and 3-deoxy-3-fluoro derivatives of di-O-acetylated methyl β-d-xylopyranoside were synthesized via 2,3-anhydropentopyranoside precursors. Methyl 2,3-anhydro-4-O-benzyl-β-d-ribopyranoside was transformed into methyl 2,3-anhydro-4-O-benzyl-β-d-lyxopyranoside in three steps. The epoxide ring opening of 2,3-anhydropentopyranosides...
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