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1,6-Anhydro-N-acetyl-β-D-glucosamine in the oligosaccharide syntheses: I. Synthesis of 3-acetate and 3-benzoate of 1,6-anhydro-N-acetyl-β-D-glucosamine via the 4-O-trityl derivative

Abstract

3-O-Acetyl and 3-O-benzoyl derivatives of 1,6-anhydro-N-acetyl-β-D-glucosamine were synthesized via its selective tritylation followed by the 3-O-acylation and removal of the trityl protective group. Tritylium trifluoromethanesulfonate, which can easily be prepared by mixing solutions of triphenylcarbinol and trimethylsilyl trifluoromethanesulfonate in an equimolar ratio, was suggested as a reagent for the effective tritylation of a secondary hydroxyl group.

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Abbreviations

1,6-AnGlcNAc:

1,6-anhydro-N-acetyl-β-D-glucosamine

CC:

column chromatography

TMS-OTf:

trimethylsilyl trifluoromethanesulfonate

TrCl:

trityl chloride

TrClO4 :

tritylium perchlorate

TrOH:

triphenylcarbinol

TrOTf:

tritylium trifluoromethanesulfonate

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Correspondence to N. E. Byramova.

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This paper is dedicated to the 70th birthday of Prof. A. Ya. Khorlin.

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Tyrtysh, T.V., Byramova, N.E. & Bovin, N.V. 1,6-Anhydro-N-acetyl-β-D-glucosamine in the oligosaccharide syntheses: I. Synthesis of 3-acetate and 3-benzoate of 1,6-anhydro-N-acetyl-β-D-glucosamine via the 4-O-trityl derivative. Russ J Bioorg Chem 26, 414–418 (2000). https://doi.org/10.1007/BF02758670

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  • DOI: https://doi.org/10.1007/BF02758670

Key words

  • carbohydrates
  • O-tritylation
  • 1,6-anhydro-N-acetyl-β-D-glucosamine
  • acylation