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Synthesis and reactions of uronic acid derivatives. V. Simple, unambiguous syntheses of methyl (methyl α-D-galactopyranosid)uronate 2-, 3-, and 4-methyl ethers

J. Hirsch, P. Kováč, and V. Kováčik

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

 

Abstract:  Partial benzoylation of methyl(methyl a-D-galactopyranosid)uronate afforded the three corresponding di-O-benzoates. Following methylation under the conditions known not to cause migration of benzoyl groups gave methyl (methyl di-0-benzoyl-0-methyl- α-D-galactopyranosid)uronates in which the location of methyl groups was determined by mass spectrometry. Debenzoylation yielded the three theoretically possible, all crystalline, monome thyl ethers of methyl (methyl α-D-galactopyranosid)uronate, of which the 3-0- and 4-0-derivatives were prepared for the first time. Preparation of methyl(methyl 4-deoxy-3-0-methyl-β-L-threo-hex-4-enopyranosid) uronate is also described.

Full paper in Portable Document Format: 286a833.pdf

 

Chemical Papers 28 (6) 833–839 (1974)

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