Practical synthesis of the 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucosides of Fmoc-serine and Fmoc-threonine and their benzyl esters

I. Carvalho, S.L. Scheuerl, K.P.R. Kartha, R.A. Field

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Mercuric bromide-promoted glycosylation of Fmoc-Ser-OBn and Fmoc-Thr-OBn with 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-d-glucopyranosyl chloride in refluxing 1,2-dichloroethane gave the corresponding β-glycosides in good yields (64 and 62%, respectively). Direct coupling of the commercially available Fmoc-Ser-OH and Fmoc-Thr-OH carboxylic acids under similar conditions gave the corresponding β-glycosides, possessing free carboxyl groups, in moderate yields (50 and 40%, respectively).
Original languageUndefined
Pages (from-to)1039-1043
Number of pages5
JournalCarbohydrate Research
Issue number10
Publication statusPublished - 1 May 2003


  • Serine
  • Threonine
  • Benzyl ester
  • Free carboxylic acid
  • Mercuric bromide
  • Glycosylation

Research Beacons, Institutes and Platforms

  • Manchester Institute of Biotechnology

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