Publication Type
Publication Type
Peer Reviewed Journal
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Authors
Garegg, Per J.,Oscarson, Stefan;
Year
1985
Month
Journal
Title
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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Published
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Volume
136
Issue
Start Page
207
End Page
13
Abstract
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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