Gold(I)-catalyzed synthesis of β-Kdo glycosides using Kdo ortho-hexynylbenzoate as donor.

Carbohydr Res

Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, China. Electronic address:

Published: August 2017

A gold(I)-catalyzed glycosylation of Kdo with glycosyl ortho-hexynylbenzoate as donor is reported. The couplings of Kdo ortho-hexynylbenzoate with a set of alcohols promoted by PPhAuOTf afford Kdo glycosides with good β-selectivities. This glycosylation method allows for the synthesis of β-Kdo monosaccharide with a C5 linker at the reducing end for subsequent conjugation to carrier proteins and arrays.

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http://dx.doi.org/10.1016/j.carres.2017.04.021DOI Listing

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