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

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.

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14

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32

Resin 10 is commercially available from Novabiochem, Switzerland; http://www.nova.ch.

41

The diisopropyl urea side product is soluble in most solvents. Therefore, DIC offers a remarkable advantage over DCC.

43

At higher reaction temperatures and higher Lewis acid concentrations TDS and benzylidene might be cleaved.