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Synthesis and reactions of uronic acid derivatives. XII. Synthesis of methyl[methyl 2-0-(2,3,4,6-tetra-0-methyl-β-D-glucopyranosyl)-3,4-di-0-methyl-α-D-galactopyranosid]uronate, a fully methylated β-D-1 → 2-linked pseudoaldobiuronic acid

J. Hirsch, P. Kováč, V. Kováčik, and V. Mihálov

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

 

Abstract: A good yield of crystalline pseudoaldobiouronic acid derivative /// was obtained by allowing to react 2,3,4,6-tetra-O-acetyl-l-bromo-l-deoxy-α-D-glucopyranose with methyl(methyl 3,4-0-isopropylidene-a-D-galactopyranosid)uronate under the condi­tions of modified Königs—Knorr synthesis of glycosides. The alcoholic hydroxyl groups in /// were regenerated by selective deisopropylidenation and subsequent deacetylation giving the crystalline methyl ester methyl glycoside V Methylation of V with methyl iodide and silver oxide in N,N-dimethylformamide, which gave the crystalline title derivative VII as the main product, was accompanied by a β-elimination reaction forming the olefinic disaccharide X. Olefin X was also synthesized and obtained crystalline by directed β-elimination reaction of /// followed by methylation of the deacetylated, crystalline olefin IX. The structures of VII. X and their synthetic precursors were confirmed by mass spectrometry.

Full paper in Portable Document Format: 305a674.pdf

 

Chemical Papers 30 (5) 674–681 (1976)

Monday, June 21, 2021

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