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Article Dans Une Revue Organic Letters Année : 2014

Synthesis of 1,2-trans-2-Acetamido-2-deoxyhomoiminosugars

Résumé

The first synthesis of 1,2-trans-homoiminosugars devised as mimics of beta-d-GlcNAc and a-d-ManNAc is described. Key steps include a regioselective azidolysis of a cyclic sulfite and a beta-amino alcohol skeletal rearrangement applied to a polyhydroxylated azepane. The beta-d-GlcNAc derivative has been coupled to serine to deliver an iminosugar C-amino acid. The two homoiminosugars demonstrate moderate glycosidase inhibition

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Dates et versions

hal-01315627 , version 1 (13-05-2016)

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Yves Blériot, Anh Tuan Tran, Giuseppe Prencipe, Jagadeesh Yerri, Nicolas Auberger, et al.. Synthesis of 1,2-trans-2-Acetamido-2-deoxyhomoiminosugars. Organic Letters, 2014, 16 (21 ), pp.5516-5519. ⟨10.1021/ol502929h⟩. ⟨hal-01315627⟩
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