A comparative study of different glycosylation methods for the synthesis of D-mannopyranosides of Nalpha-fluorenylmethoxycarbonyl-trans-4-hydroxy-L-proline allyl ester |
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| Authors: | Lee Dong Jun Kowalczyk Renata Muir Victoria J Rendle Phillip M Brimble Margaret A |
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| Affiliation: | Department of Chemistry, The University of Auckland, 23 Symonds Street, Auckland, New Zealand. |
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| Abstract: | The synthesis of Nalpha-fluorenylmethoxycarbonyl-trans-4-hydroxy-4-O-[(2,3,4,6-tetra-O-acetyl)-alpha-d-mannopyranosyl]-l-proline allyl ester and Nalpha-fluorenylmethoxycarbonyl-trans-4-hydroxy-4-O-[(2,3,4,6-tetra-O-benzoyl)-alpha-d-mannopyranosyl]-l-proline allyl ester is described. Glycosylation using K?nigs-Knorr conditions with a benzoyl protected glycosyl donor provided the optimum method. Removal of the allyl ester gave two mannosylated building blocks suitable for solid phase glycopeptide synthesis. |
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| Keywords: | Sugar amino acids trans-4-Hydroxy-proline Mannose O-Glycosylation Vaccines and C-lectins |
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