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

Abstract

Methyl and benzyl (ethyl 3,4-di-O-benzyl-2-O-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 BH3.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 1H, 13C and 2D NMR, alongside MS and IR analysis.

Keywords

• glucuronic acid
• TEMPO
• regioselective
• oxidation
• NMR