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© 2015 Elsevier Ltd. All rights reserved. The methyl glycosides of 3-deoxy-3-amino-d-glycero-l-gulo-heptose, 3-deoxy-3-amino-d-glycero-d-galacto-heptose, 3-deoxy-3-amino-d-glycero-l-allo-heptose and 3-deoxy-3-amino-d-glycero-d-allo-heptose were prepared from the corresponding d-aldopentoses via a seven step synthetic sequence. The doubly diastereoselective conjugate additions of the requisite antipode of lithium N-benzyl-N-(α-methylbenzyl)amide to four diastereoisomeric d-aldopentose-derived α,β-unsaturated esters and in situ enolate oxidation with the requisite antipode of camphorsulfonyloxaziridine (CSO) were used as the key, stereodefining steps. Sequential protection of the C(2)-hydroxyl group within the resultant α-hydroxy-β-amino esters and partial reduction of the ester functionality furnished the corresponding β-amino aldehydes. Subsequent N- and O-deprotection gave the target compounds (as the corresponding methyl pyranosides and/or methyl furanosides) in good yields and high diastereoisomeric purity.

Original publication

DOI

10.1016/j.tetasy.2015.11.004

Type

Journal article

Journal

Tetrahedron Asymmetry

Publication Date

15/01/2016

Volume

27

Pages

31 - 42