Tetrahedron p. 6033 - 6038 (1986)
Update date:2022-08-02
Topics:
Herrera, Lopez F. J.
Gonzalez, Pino M. S.
A practical synthetic route to 2-deoxy-3-O-methyl-1,4-aldonolactones is achieved.Isopropylidene derivatives of aldehyde sugars 1, (free or in lactol form), reacted with methyl hydrogen malonate to give α,β-unsaturated esters 2.In the case of lactols, the R group in 2 is not identical to the R in 1 (epimerisation occurs).Base-catalysed addition of methanol to the esters 2 afforded the epimeric ethers 3, acid hydrolisis of which yielded the 2-deoxy-3-O-methyl-1,4-aldonolactones 4.Degradation of the sugar chain permitted the assignment of the absolute configuration on C-3.
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