Chinese Journal of Organic Chemistry >
Efficient Synthesis of Allolactose
Received date: 2013-12-22
Revised date: 2014-01-13
Online published: 2014-02-10
Supported by
Project supported by the National Natural Science Foundation of China (No. 21172257) and the National S&T Pillar Program of China (Nos. 2012BAK25B03-01, 2011AA10A206).
Allolactose (β-D-galactopyranosyl-(1→6)-α,β-D-glucopyranose) is a reducing disaccharide playing important biological role in bacterial metabolism. Two synthetic methods of allolactose including regioselective glycosylation and stepwise synthesis were investigated using D-glucose and D-galactose as the starting materials. The later approach involved a five-spot strategy, 44% overall yields and all the intermediates were easily to be purified, making the route suitable for large scale preparation of the target compound. All the compounds were characterized by NMR and HRMS spectra.
Key words： allolactose; D-glucose; D-galactose; synthesis
Jiang Rui , Liang Xiaomei , Jin Shuhui , Zhang Jianjun , Wang Daoquan . Efficient Synthesis of Allolactose[J]. Chinese Journal of Organic Chemistry, 2014 , 34(5) : 926 -932 . DOI: 10.6023/cjoc201312028
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