Synthesis of a C-Glycoside Analog of the Tumor-Associated Tn Antigen

Christoph H. Röhrig; Mohamed Takhi; Richard R. Schmidt

doi:10.1055/s-2001-15144

Synlett 2001; 2001(7): 1170-1172
DOI: 10.1055/s-2001-15144

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Synthesis of a C-Glycoside Analog of the Tumor-Associated Tn Antigen

Christoph H. Röhrig^* , Mohamed Takhi, Richard R. Schmidt

^*Department of Chemistry, University of Konstanz, Fach M 725, 78457, Konstanz, Germany; Fax + 49-75 31-88-31 35; E-mail: richard.schmidt@uni-konstanz.de

Abstract

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A hydrolytically stable carbon analogue of the Tn antigen (GalNAcα1-O-Ser) has been efficiently synthesized employing a Wittig-Horner reaction of C-linked aldehyde 3 with glycine derived phosphonate 4, followed by asymmetric hydrogenation of the 2-acetamido-sugar residue containing α-acylaminoacrylate 5.

C-glycosides - Tn antigen - glycopeptide analogues - 2-deoxy-2-acetamido galactosamine - asymmetric hydrogenation

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