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Peer Reviewed Journal
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Garegg, Per J.,Oscarson, Stefan;
1985
A synthesis of 8-methoxycarbonyloct-1-yl O-a-D-galactopyranosyl-(1 -> 3)-O-b-D-galactopyranosyl-(1 -> 4)-2-acetamido-2-deoxy-b-D-glucopyranoside
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136
207
13
Halide-assisted glycosylation, using a non-participating 2-substituent (benzyl) in the glycosyl halide, was used to obtain the a-D-galactosyl linkage and Ag triflate promotion with a participating 2-substituent (benzoyl) was used to obtain the b-D-galactosyl linkage in a facile synthesis of the title trisaccharide deriv. The synthesis also incorporates the use of stable thioglycoside intermediates, easily converted into the appropriate galactosyl bromides, as well as regioselective, reductive and acid-catalyzed openings of cyclic acetals and orthoesters, resp., to obtain the required intermediates. [on SciFinder (R)]
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