Novel linker <i>N</i>-({[4-(3-aminopropylcarbamoyl)phenyl]ethysulphanyl}methyl)-2-phenylacetamide 87 has been developed which is compatible with a range of reactions (e.g. base oxidation, alkylation), can be cleaved under mild conditions and has the ability to release alcohols and amines. An efficient synthesis of the linker has been devised and attachment to a variety of solid supports (Tentagel, polystyrene) has been achieved. (Fig. 9966A). As a general building block 2-acetamido-3, 4-di-<i>O</i>-acetyl-2-deoxy-<i>N</i>-(fluoren-9-yl-methoxycarbonyl)-b-D-glucopyranosylamine 106 was synthesised in gram quantities from <i>N</i>-acetylglucosamine in 8 steps. The saccharide was linked through the 6-hydroxyl group onto carboxy-Tentagel <i>via </i>linker 87 in excellent yield and extension of the glycoside amino group provides a route towards the synthesis of glycopeptides. (Fig. 9966B). As an alternative, sugar building block 2-acetamido-2-deoxy-<i>N</i>-(benzyloxycarbonyl)-b-D-glucopyranosylamine 129 was synthesised from <i>N</i>-acetylglucosamine in 5 steps. The saccharide was attached onto carboxy-Tentagel <i>via </i>linker 87 and has been used in initial studies into the esterification reactions to generate a small library of compounds. (Fig. 9966C).
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:661094 |
| Date | January 2000 |
| Creators | Rice, David Cunningham |
| Publisher | University of Edinburgh |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Source | http://hdl.handle.net/1842/11310 |
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