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Issue 44, 2013
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Synthesis of oseltamivir and tamiphosphor from N-acetyl-D-glucosamine

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Abstract

Using N-acetyl-D-glucosamine as a starting material, the anti-influenza drugs oseltamivir and tamiphosphor were synthesized via a pivotal intermediate of aldehyde 8. An intramolecular Horner–Wadsworth–Emmons reaction was utilized to construct the highly functionalized cyclohexene ring. The existing N-acetyl group was transformed into an azido group for the subsequent aziridination, followed by implantation of a 3-pentoxy group of the desired stereochemistry.

Graphical abstract: Synthesis of oseltamivir and tamiphosphor from N-acetyl-d-glucosamine

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Publication details

The article was received on 08 Aug 2013, accepted on 17 Sep 2013 and first published on 17 Sep 2013


Article type: Paper
DOI: 10.1039/C3OB41622D
Citation: Org. Biomol. Chem., 2013,11, 7687-7699
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    Synthesis of oseltamivir and tamiphosphor from N-acetyl-D-glucosamine

    C. Chen and J. Fang, Org. Biomol. Chem., 2013, 11, 7687
    DOI: 10.1039/C3OB41622D

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