Formal Synthesis of 3-Deoxy-d-manno-Octulosonic Acid (KDO) and 3-Deoxy-d-arabino-2-heptulosonic Acid (DAH)

2012/12/21 by Kwok Mong, Kwok Kong Tony Mong, Tapan Kumar Pradhan +2
Chemistry · Biochemistry, Genetics and Molecular Biology · Nursing · #Carbohydrate Chemistry and Synthesis #Glycosylation and Glycoproteins Research #Microbial Metabolites in Food Biotechnology

paper · doi:10.1055/s-0032-1317932

Abstract

Practical synthetic routes to 3-deoxy-<sc>d</sc>-<i>manno</i>-octulo­sonic acid (KDO) and 3-deoxy-<sc>d</sc>-<i>arabino</i>-2-heptulosonic acid (DAH) from common sugar substrates are reported. Chain homologation of the sugar substrates was accomplished by Wittig olefination and Corey–Fuchs alkynylation. A new cyclization strategy was investigated to access the desired pyranosyl isomer of the KDO target.

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