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Efficient Large Scale Syntheses of 3-Deoxy-D-manno-2-octulosonic acid (Kdo) and Its Derivatives
Yingle Feng1, Jie Dong1, Fangyuan Xu1
1School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, Shaanxi 710119, P. R. China.
Abstract:
An efficient method to rapidly synthesize 3-deoxy-D-manno-2-octulosonic acid (Kdo) and its derivatives in large scale has been developed. Starting from D-mannose, the di-O-isopropylidene derivative of Kdo ethyl ester was prepared in three steps on a scale of more than 40 g in one batch in an overall yield of 75-80% without any intermediate purification. Kdo, Kdo glycal, and 2-acetylated Kdo ester were synthesized quickly in high yield from a di-O-isopropylidene derivative of Kdo ethyl ester. 2-Deoxy-β-Kdo ester was obtained with high stereoselectivity via the epimerization of the α-isomer using t-BuOH as a proton source.
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