✦ LIBER ✦

A synthesis of 8-methoxycarbonyloct-1-yl O-α-d-galactopyranosyl-(1→3)-O-β-d-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-d-glucopyranoside

✍ Scribed by Per J. Garegg; Stefan Oscarson

Publisher: Elsevier Science
Year: 1985
Tongue: English
Weight: 480 KB
Volume: 136
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(85)85197-1

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✦ Synopsis

Halide-assisted glycosyIation, using a non-p~icipating Z-substituent (benzyl) in the glycosyl halide, was used to obtain the ~-D-gaiactosyl linkage and silver triflate promotion with a participating 2-substituent (benzoyl) was used to obtain the /3-D-galactosyl linkage in a facile synthesis of the title trisaccharide derivative. The synthesis also incorporates the use of stable thioglycoside intermediates, easily converted into the appropriate gaiactosyi bromides, as we11 as regioselective, reductive and acid-catalysed openings of cyclic acetals and orthoesters, respectively, to obtain the required intermediates.

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