Asymmetric syntheses of the methyl glycosides of 2-deoxy-2-aminohexoses: D-allosamine, D-mannosamine, D-idosamine and D-talosamine

Journal article

A range of the methyl glycosides of 2-deoxy-2-aminohexoses, comprising d-allosamine, d-mannosamine, d-idosamine and d-talosamine, were prepared from the corresponding d-aldopentoses via a seven step synthetic sequence. The doubly diastereoselective conjugate addition of the requisite antipode of lithium N-benzyl-N-(α-methylbenzyl)amide and in situ enolate oxidation with the requisite antipode of camphorsulfonyloxaziridine (CSO) was used as the key, stereodefining step. Sequential reduction of...

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Authors: Davies, S; Fletcher, A; Foster, E; Lee, J; Roberts, P

• Publication status: Published
• Journal: TETRAHEDRON
• Volume: 70
• Issue: 40
• Pages: 7106-7119
• Publication date: 2014-10-07
• DOI: 10.1016/j.tet.2014.06.019
• EISSN: 1464-5416
• ISSN: 0040-4020
• Language: English
• Keywords: 2-Deoxy-2-aminohexoses; Asymmetric synthesis; Aminosugars; Lithium amide; Conjugate addition