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Chemical and physical studies on oligosaccharides. Isolation, configurations, and conformations of the per-O-acetyl-O-β-D-glucopyranosyl-(1→3)-D-arabinoses by María E. Gelpi; Raúl A. Cadenas is a Biochemistry, Genetics and Molecular Biology article available to read on EtoBox.

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The reaction of octa-O-acetylcellobiononitrile with sodium methoxide, and acetylation of the resulting mixture, afforded the anomeric peracetates of O-/?-Dglucopyranosyl-( I -+3)-D-arabinopyranose and ~-/3-D-glUCOpyranOSy1-(1+3)-D-arabinofuranose, which were isolated by fractional recrystallization. Their structures, anomeric configurations, and conformations were studied by chemical, optical, and spectroscopic methods. RESULTS ## AND DISCUSSION From the chemical point of view, it has now been observed that compounds 2 and 4 are readily interconverted by anomerization reagents, whereas compounds 3 and 5 are extensively decomposed, and not unambiguously interconverted. A /3-pyranose anomer can be obtained by heating the corresponding a-pyranose with acetic anhydride-acetic acid and a catalytic amount of sulfuric acid3. When 2 was treated with this mixture, compound 4 was obtained in 50% yield as the only

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Author

María E. Gelpi; Raúl A. Cadenas

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0008-6215)

Published

1981

Language

EN

Field

Biochemistry, Genetics and Molecular Biology (Life Sciences)