Improved synthesis of d-allothreonine derivatives from l-threonine

Abstract

The improved synthesis of protected d-allothreonine derivatives [Fmoc-d-alloThr(tBu)-OH (1) and Fmoc-d-alloThr-OtBu (2)] is described. The epimerization of cheap l-threonine (l-Thr) (3) with catalytic salicylaldehyde afforded a mixture of l-Thr (3) and d-alloThr (4) and separation of ammonium salt gave d-alloThr (4) in 96% de. The chemoselective deprotection of tert-butyl ether or tert-butyl ester of Fmoc-d-alloThr(tBu)-O tBu (5) easily succeeded in converting Fmoc-d-alloThr( tBu)-OH (1) or Fmoc-d-alloThr-OtBu (2), respectively. © 2013 Elsevier Ltd. All rights reserved.