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Synthèse, Conformation et Affinité Tréhalasique Des α-D-glucopyranosyl-α-d-xylopyranoside, α-D-glucopyranosyl-α-d-mannopyranoside et α-D-allopyranosyl-α-d-glucopyranoside by Édith Bar-Guilloux; Jacques Defaye; Hugues Driguez; Daniel Robic is a Biochemistry, Genetics and Molecular Biology article available to read on EtoBox.

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Recu le 30 juin 1975; accept6 le 15 septembre 1975) AB!?rRAcr or-D-Glucopyranosyl a-D-xylopyranoside has been synthesized in 49% yield by treatment of 2,3,4-tri-O-benzyl-cx-D-xylopyranosyl bromide with 2,3,4,6-tetra-0acetyl-D-glucopyranose in nitromethane-benzene with mercuric cyanide ard bromide, followed by catalytic hydrogenolysis and O-deacetylation. Condensation of 2,3,4,6tetra-O-benzyl-D-glucopyranose with 2,3,4,6-tetra-O-acetyl-cc-D-mannopyranosyl bromide in acetonitrile-dichloromethane with mercuric cyanide, followed by catalytic hydrogenolysis and O-deacetylation, gave a-D-glucopyranosyl a-D-mannopyranoside and /I-D-glucopyranosyl #l-D-mannopyranoside in 44 and 25% yield, respectively. The mixture was resolved by column chromatography of the fully acetylated deriv-atives\_ Selective acetylation of the di-O-benzylidene derivative of trehalose with N-acetylimidazole, followed by oxidation with dimethyl sulfoxide-acetic anhydride at C-3 and stereoseIective reduction gave, after removal of the protecting groups, a-D-aliopyranosyl a-D-glucopyranoside in 20% overall yield. The structure of the compounds was confirmed by IH-and 13C-n.m.r., and mass spectrometry. or-D-Glucopyranos

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Author

Édith Bar-Guilloux; Jacques Defaye; Hugues Driguez; Daniel Robic

Publisher

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

Published

1975

Language

FR

Field

Biochemistry, Genetics and Molecular Biology (Life Sciences)