Title of article :
Efficient synthesis of (2R,3S)-2-amino-3-(benzyloxy)-4,4,4-trifluorobutanoic acid (4,4,4-trifluoro-OBn-d-allothreonine)
Author/Authors :
Zeng، نويسنده , , Chun-min and Kerrigan، نويسنده , , Sean A. and Katzenellenbogen، نويسنده , , John A. and Slocum، نويسنده , , Connie and Gallacher، نويسنده , , Kyla and Shomali، نويسنده , , Maysoun and Lyttle، نويسنده , , C. Richard and Hattersley، نويسنده , , Gary and Miller، نويسنده , , Chris P.، نويسنده ,
Abstract :
An efficient synthesis of the non-proteinogenic amino acid (2R,3S)-4,4,4-trifluoro(OBn)-threonine is described. Starting with commercially available (S)-Garner’s aldehyde, the desired amino acid was prepared as its hydrochloride salt in five steps and an overall yield of 33% (59% based on recovered starting material). The utility of this unusual amino acid was demonstrated by its elaboration into a potent and selective androgen.
