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A series of 4,6-O-benzylidene-protected 2-O-benzyl-3-deoxy-3-fluoro- and 3-O-benzyl-2-deoxy-2-fluorogluco- and mannopyranosyl thioglycosides were synthesized and their coupling reactions with a series of alcohols, on preactivation with 1-benzenesulfinylpiperidine and trifluoromethanesulfonic anhydride, investigated. In all cases, the selectivities were lower than those observed with the corresponding simple 4,6-O-benzylidene 2,3-di-O-benzylgluco- and mannopyranosyl thioglycosides. This leads to the conclusion that the high beta-selectivity observed with 4,6-O-benzylidene 2,3-di-O-benzylmannopyranosyl donors under the same conditions is in large part derived from the compression of the O2-C2-C3-O3 torsion angle on going from the intermediate covalent glycosyl triflate to the oxacarbenium ion, as compared to the relaxation of this torsion angle in the gluco series.

journal of organic chemistry

4,6-<i>O</i>-Benzylidene-Directed β-Mannopyranosylation and α-Glucopyranosylation: The 2-Deoxy-2-fluoro and 3-Deoxy-3-fluoro Series of Donors and the Importance of the O2−C2−C3−O3 Interaction

4,6-O-Benzylidene-Directed β-Mannopyranosylation and α-Glucopyranosylation: The 2-Deoxy-2-fluoro and 3-Deoxy-3-fluoro Series of Donors and the Importance of the O2−C2−C3−O3 Interaction