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Synthesis 2001(15): 2263-2272
DOI: 10.1055/s-2001-18441
PAPER
© Georg Thieme Verlag Stuttgart · New York

Solid Phase Syntheses of Oligomannosides and of a Lactosamine Containing Milk Trisaccharide Using a Benzoate Linker

Matthias Grathwohla, Richard R. Schmidt*b
a Alchemia Pty. Ltd., 3 Hi-Tech Court, Brisbane Technology Park, Eight Mile Plains 4113, Qld, Australia.
b Fachbereich Chemie, Universität Konstanz, Fach M 725, 78457 Konstanz, Germany
Fax: +49(7531)883135; e-Mail: richard.schmidt@uni-konstanz.de;
Further Information

Publication History

Received 25 July 2001
Publication Date:
05 August 2004 (online)

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Abstract

Galactose and mannose building blocks 9 and 12 were designed for the solid phase synthesis of oligosaccharides (SPOS). Both compounds were employed after condensation with benzoic acid function containing resin 10 in SPOS of human milk trisaccharide 1 and oligomannosides 2-4 (α-(1Æ2)-linked hexamer). Thus, in this approach a special linker development was not required and with the temporary protective groups phenoxyacetyl (PA) and 9-fluorenylmethoxycarbonyl (Fmoc) as part of compounds 7-12 the strategy offers the additional advantage of having the anomeric centre at the reducing end available for further manipulations.

Key words

solid-phase synthesis - Fmoc-protected hydroxy groups - glycosidations - trichloroacetimidates - oligosaccharides.