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1 2005

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Synthesis of C-Glycosidic Galacturonates Suitable as Glycosyl Acceptors

Vogel C., Farouk M., Michalik M., Reinke H., Jarosz S.

Polish Journal of Chemistry

2005

Vol. 79 / nr 2

251-265

Methyl 3,4,5-tri-O-acetyl-2,6-anhydro-7,8,9-trideoxy-D-glycero-L-galacto-non-8-enonate (5) was obtained by different routes starting from D-galactose and D-galacturonic acid, respectively. Exploring several protecting group manipulations, an effective route was found out for the preparation of methyl 2,6-anhydro-5-O-benzyl-7,8,9-trideoxy- D-glycero-L-galacto-non-8-enonate (15) which is one of the key compounds in this synthetic program. Finally, selective benzylation via 3,4-O-butylstannyl intermediates resulted in methyl (16) and benzyl (17) 2,6-anhydro-4,5-di-O-benzyl-7,8,9-trideoxy-Dglycero- L-galacto-non-8-enonate both suitable as acceptors in glycosylation reactions. The chemical structure of a great number of intermediates was investigated by X-ray diffraction studies.