590410-69-8Relevant articles and documents
Structure-Guided Tuning of a Hydroxynitrile Lyase to Accept Rigid Pharmaco Aldehydes
Hong, Ran,Li, Fu-Long,Lin, Guo-Qiang,Lin, Zuming,Xu, Jian-He,Yu, Hui-Lei,Zheng, Yu-Cong
, p. 5757 - 5763 (2020/06/09)
The chiral vicinal C-O/C-N bifunctional groups generated from enzymatic hydrocyanation represents a useful methodology. However, construction of the pharmacophore of β2-adrenoreceptor agonists with this method remains a great challenge because of complete racemization of the benzylic alcohol during deprotection of the acetal groups. In this study, structure-guided redesign of a hydroxynitrile lyase originating from Prunus communis (PcHNL5) enables a highly enantioselective hydrocyanation of rigid benzo-ketal aldehyde which was proved to be resistant against racemization during the deprotection step, with dramatically improved productivity (>95% conversion vs 2-adrenoreceptor agonist, in an optically pure form (>99% ee) with an overall yield of 54%, which is the highest value reported.
A convenient synthesis of (R)-salmeterol via Rh-catalyzed asymmetric transfer hydrogenation
Liu, Juntao,Zhou, Di,Jia, Xian,Huang, Ling,Li, Xingshu,Chan, Albert S.C.
, p. 1824 - 1828 (2008/12/22)
(R)-Salmeterol was synthesized in eight steps with salicaldehyde as the starting material. The key chiral intermediate, alcohol 5, was prepared via Rh-catalyzed asymmetric transfer hydrogenation with (S,S)-PEG-BsDPEN or (S,S)-TsDPEN ligand and sodium formate as the hydrogen donor under mild conditions.
A mild, enantioselective synthesis of (R)-salmeterol via sodium borohydride-calcium chloride asymmetric reduction of a phenacyl phenylglycinol derivative
Bream, Robert N.,Ley, Steven V.,McDermott, Benjamin,Procopiou, Panayiotis A.
, p. 2237 - 2242 (2007/10/03)
A short and efficient enantioselective route to (R)-salmeterol involving asymmetric reduction of a phenylglycinyl ketone derivative followed by reductive amination of the resulting amino alcohol and hydrogenolysis is described.