Stereoselective synthesis of the C-analogue of β-d-glucopyranosyl serine

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Luigi Lay, Morten Meldal, Francesco Nicotra, Luigi Panza and Giovanni Russo


Abstract

The [2,3]-Wittig sigmatropic rearrangement of an appropriate glucose derivative followed by further chemical modification afforded stereoselectively the C-analogue of β-D-glucopyranosyl serine.


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