Chiral 2-trichloromethyloxazolines 4,5-cis-annulated to a carbohydrate fragment were synthesized on the basis of levoglucosenone. The synthesized compounds were converted by acid hydrolysis into 4-substituted 3-amino-1,6-anhydro-3-deoxy-β-D-mannopyranoses. Intramolecular amination of allyl trichloroacetimidates by electrophilic reagents was used to construct the oxazoline ring. It was established that trichloroacetimidates containing an epoxide ring in α,β-positions spontaneously undergo recyclization with the formation of an oxazoline ring.
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The authors are grateful to the Collective Use Center “Khimiya”, Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences, the Regional Center for Collective Use “Agidel” of the Ufa Federal Research Center of the Russian Academy of Sciences for analytical and spectral studies, and Circa Group (Melbourne, Australia) for the generous gift of levoglucosenone.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(4/5), 199–205
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Sharipov, B.T., Davidova, A.N. & Valeev, F.А. cis-Annulation of an oxazoline fragment to levoglucosenone and the synthesis of 4-substituted 3-amino-1,6-anhydro-3-deoxy-β-D-mannopyranose. Chem Heterocycl Comp 58, 199–205 (2022). https://doi.org/10.1007/s10593-022-03073-y
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DOI: https://doi.org/10.1007/s10593-022-03073-y