Reaction of 1,2- trans-glycosyl acetates with thiourea: a new entry to 1-thiosugars

The reaction of 1,2- trans-glycosyl acetates with thiourea under boron trifluoride etherate catalysis affording acetylated S-glycosyl isothiourea derivatives is described. The isothiourea derivatives obtained can be readily transformed into the desired 1-thiosugar derivative by reaction with triethy...

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Bibliographic Details
Published in:Tetrahedron letters 2003-10, Vol.44 (43), p.7961-7964
Main Authors: Ibatullin, Farid M., Shabalin, Konstantin A., Jänis, Janne V., Shavva, Alexander G.
Format: Article
Language:English
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Summary:The reaction of 1,2- trans-glycosyl acetates with thiourea under boron trifluoride etherate catalysis affording acetylated S-glycosyl isothiourea derivatives is described. The isothiourea derivatives obtained can be readily transformed into the desired 1-thiosugar derivative by reaction with triethylamine and subsequent alkylation or acylation of the in situ formed 1-thioaldose. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2003.08.120