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Efficient synthesis of (2R,3S)-2-amino-3-(benzyloxy)-4,4,4-trifluorobutanoic acid (4,4,4-trifluoro-OBn-d-allothreonine)

✍ Scribed by Chun-min Zeng; Sean A. Kerrigan; John A. Katzenellenbogen; Connie Slocum; Kyla Gallacher; Maysoun Shomali; C. Richard Lyttle; Gary Hattersley; Chris P. Miller

Publisher: Elsevier Science
Year: 2010
Tongue: French
Weight: 425 KB
Volume: 51
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2010.07.147

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✦ Synopsis

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.

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