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Synthesis 2001; 2001(3): 0419-0422
DOI: 10.1055/s-2001-11443
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A General Procedure for Conversion of S-Glycosyl Isothiourea Derivatives into Thioglycosides, Thiooligosaccharides and Glycosyl Thioesters

Farid M. Ibatullin* , Stanislav I. Selivanov, Alexander G. Shavva
  • *Molecular and Radiation Biophysics Division, Petersburg Nuclear Physics Institute, Gatchina, 188300 Russia; Tel + (7)81 27 14 60 56; Fax + (7)81 27 13 23 03; E-mail: ibatullin@omrb.pnpi.spb.ru
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Publication Date:
31 December 2001 (online)

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A simple procedure for conversion of S-glycosyl isothiourea derivatives into thioglycosides by promotion with triethylamine is described. The reaction conditions allow the synthesis of glycosyl thioesters and some thioglycosides, which cannot be prepared using the traditional approach. The procedure has been successfully applied for preparation of thiooligosaccharides, shown by syntheses of methyl 4-thio-α-cellobioside and methyl 4-thio-α-lactoside derivatives.

alkyl halides - carbohydrates - thioglycosides - thiooligosaccharides - thioesters

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