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Synthesis and reactions of uronic acid derivatives. IV. Unambiguous synthesis of methyl (methyl α- and β-D-glucopyranosid)uronate

P. Kováč, J. Alföldi, and M. Košík

Institute of Chemistry, Slovak Academy of Sciences, 809 33 Bratislava

 

Abstract: Optimum conditions for the oxidn. of the primary OH group of Me 2,3,4-tri-O-methyl-α-D-glucopyranoside to the corresponding uronic acid with CrO3 and dil. H2SO4 in Me2CO were detd. Me 2,3,4-tri-O-benzoyl- and -benzyl-α-D-glucopyranoside and Me 2,3,4-tri-O-acetyl- and -benzyl-β-D-glucopyranoside were oxidized to give uronic acids which were esterified with CH2N2. Deblocking gave Me (Me α- and β-D-glucopyranosid)uronates.

Full paper in Portable Document Format: 286a820.pdf

 

Chemical Papers 28 (6) 820–832 (1974)

Thursday, February 25, 2021

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