Asymmetric synthesis of suitably protected γ-hydroxy-aza-β3-homothreonine building blocks
摘要:
An efficient and easily applicable method for the enantioselective synthesis of gamma-Hydroxy aza-beta(3)-homothreonine (aza-beta(3)-Hyht) has been established. The method involves stereoselective reductive amination of glyoxylic acid and the corresponding Fmoc protected chiral hydrazine. A stereoselectivity of 99% was achieved for each step using (R)-2,3-O-isopropylideneglyceraldehyde as the chiral auxiliary. This new synthetic monomer is a useful building block for the solid-phase synthesis of new peptidomimetics. (C) 2009 Elsevier Ltd. All rights reserved.