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Methyl and Benzyl (Ethyl 3,4-di-<i>O</i>-benzyl-2-<i>O</i>-benzoyl-1-thio-β-<span style="font-variant: small-caps">d</span>-glucopyranosyl)uronate
oleh: Hannah S. Wootton, Gavin J. Miller
Format: | Article |
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Diterbitkan: | MDPI AG 2024-07-01 |
Deskripsi
Methyl and benzyl (ethyl 3,4-di-<i>O</i>-benzyl-2-<i>O</i>-benzoyl-1-thio-β-D-glucopyranosyl)uronate were synthesised from a protected thioglycoside in three steps. A regioselective ring opening of the benzylidene acetal with BH<sub>3</sub><sup>.</sup>THF generated C6-OH material, which was subsequently oxidised using biphasic TEMPO/BAIB conditions. The resultant uronic acid was esterified with either a methyl or benzyl moiety. The products were obtained on a multigram scale and fully characterised by <sup>1</sup>H, <sup>13</sup>C and 2D NMR, alongside MS and IR analysis.