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Tin-mediated equilibration of the benzoate esters of methyl 4,6-O- benzylidene-α-D-glucopyranoside

Bredenkamp M.W. ; Spies H.S.C. (2000)


The selective dibutyltin oxide-mediated benzoylation of methyl 4,6-O- benzylidene-α-D-glucopyranoside at position 2 is not a post-acylation phenomenon as is the case with the equivalent benzoylation of phenylethyleneglycol. 1H NMR temperature studies have shown that such equilibration occurs only above 85 °C in toluene-d8 for the glucopyranoside.

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