Synthesis and structural studies of anomeric 2,3,4,6-tetra-O-acetyl-5-thio-D-glucopyranosyl azides

Marianna Katona Strumpel, Jürgen Buschmann, László Szilágyi, Zoltán Györgydeák

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8 Citations (Scopus)

Abstract

Two methods are presented for the preparation of the α and β anomers of 2,3,4,6-tetra-O-acetyl-5-thio-D-glucopyranosyl azide. These methods are comparable in yield, but the one that converts a glucopyranosyl bromide into the azide is preferable because of easier purification. After chromatographic separation, the α and β anomers were analysed by NMR spectroscopy. The crystal and molecular structure of the β anomer was determined by X-ray diffraction. It crystallises in space group P21 [a=11.729(3), b=7.305(3), c=11.363(3)A, β=107.63(5)°, Z=2]. The hexopyranose ring of the β anomer assumes a 4C1 conformation and the orientation of the azido group is compatible with the requirements of the exo-anomeric effect. This geometry is compared to that of other similar structures. Copyright (C) 1999 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)91-97
Number of pages7
JournalCarbohydrate Research
Volume318
Issue number1-4
DOIs
Publication statusPublished - May 31 1999

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Keywords

  • 5-Thio-D-glucopyranose
  • Anomeric azides
  • NMR
  • X-ray crystal structure

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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