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  • Title: Synthetic receptor analogues: preparation and calculated conformations of the 2-deoxy, 6-O-methyl, 6-deoxy, and 6-deoxy-6-fluoro derivatives of methyl 4-O-alpha-D-galactopyranosyl-beta-D-galactopyranoside (methyl beta-D-galabioside).
    Author: Kihlberg J, Frejd T, Jansson K, Sundin A, Magnusson G.
    Journal: Carbohydr Res; 1988 May 15; 176(2):271-86. PubMed ID: 3416321.
    Abstract:
    The 2-deoxy (7), 6-O-methyl (15), 6-deoxy (22), and 6-deoxy-6-fluoro (31) derivatives of methyl beta-D-galabioside (1) have been synthesised. Thus, 7 was prepared by xanthate reduction using tributyltin hydride, whereas 22 was obtained by catalytic hydrogenation of a 6-deoxy-6-iodogalabioside. Regioselective monofluorination of methyl 2,3-di-O-benzoyl-beta-D-galactopyranoside with Et2NSF3 and subsequent alpha-D-galactosylation provided 31. Molecular mechanics calculations yielded similar conformations for 1, 7, 15, 22, and 31 with differences in phi H and psi H of less than 5 degrees. No indications of intramolecular hydrogen bonds, as displayed by 1 in the crystal, were found for 7, 15, 22, or 31.
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