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© 2014 Elsevier Ltd 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 the resultant α-hydroxy-β-amino esters and oxidative cleavage of the C(1)–C(2) diol unit furnished the corresponding α-amino aldehydes. Subsequent N- and O-deprotection gave the target compounds (as mixtures of anomers) in good yield and high diastereoisomeric purity.

Original publication

DOI

10.1016/j.tet.2014.06.019

Type

Journal article

Journal

Tetrahedron

Publication Date

01/01/2014

Volume

70

Pages

7106 - 7119