Beilstein J. Org. Chem.2014,10, 1808–1816, doi:10.3762/bjoc.10.190
C12, the more abundant 3 was condensed either with (S)- or (R)-α-methoxyphenylacetic acid (MPA) [15] to give bis-MPA esters 3a and 3b. The δΔ values for the 2-en-1,4-diol moiety do not hold a diagnostic value because this region is under the influence of overlapping anisotropic effects by the flanking
Beilstein J. Org. Chem.2014,10, 1686–1691, doi:10.3762/bjoc.10.177
carbonyl group at the termini has been carried out. The carbonyl group has been exploited for the multivalent conjugation to a sample saccharide by reductive amination and alkoxyamine conjugation.
Keywords: bis-MPA; carbohydrates; dendrons; levulinic acid; multivalency; multivalent glycosystems
reactions with levulinic acid (15). Building blocks 13 and 14 were synthesized starting from bis-(hydroxymethyl)propionic acid (bis-MPA) and bromo-1-pentene [11] in one and four steps, respectively.
L-Fucose derivatives synthesis
α-L-(2-Aminoethyl) fucopyranoside (4) and α-O-L-fucopyranosyloxyamine (5) were
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Graphical Abstract
Figure 1:
Synthesized G0, G1 and G2 dendrons and functionalized saccharides used for carbonyl conjugation.