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

Chun Min Zeng; Sean A. Kerrigan; John A. Katzenellenbogen; Connie Slocum; Kyla Gallacher; Maysoun Shomali; C. Richard Lyttle; Gary Hattersley; Chris P. Miller

doi:10.1016/j.tetlet.2010.07.147

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

Chun Min Zeng, Sean A. Kerrigan, John A. Katzenellenbogen, Connie Slocum, Kyla Gallacher, Maysoun Shomali, C. Richard Lyttle, Gary Hattersley, Chris P. Miller

Chemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English (US)
Pages (from-to)	5361-5363
Number of pages	3
Journal	Tetrahedron Letters
Volume	51
Issue number	41
DOIs	https://doi.org/10.1016/j.tetlet.2010.07.147
State	Published - Oct 13 2010

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2010.07.147

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

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.",

author = "Zeng, {Chun Min} and Kerrigan, {Sean A.} and Katzenellenbogen, {John A.} and Connie Slocum and Kyla Gallacher and Maysoun Shomali and Lyttle, {C. Richard} and Gary Hattersley and Miller, {Chris P.}",

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doi = "10.1016/j.tetlet.2010.07.147",

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volume = "51",

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journal = "Tetrahedron Letters",

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T1 - Efficient synthesis of (2R,3S)-2-amino-3-(benzyloxy)-4,4,4- trifluorobutanoic acid (4,4,4-trifluoro-OBn-d-allothreonine)

AU - Zeng, Chun Min

AU - Kerrigan, Sean A.

AU - Katzenellenbogen, John A.

AU - Slocum, Connie

AU - Gallacher, Kyla

AU - Shomali, Maysoun

AU - Lyttle, C. Richard

AU - Hattersley, Gary

AU - Miller, Chris P.

PY - 2010/10/13

Y1 - 2010/10/13

N2 - 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.

AB - 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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SN - 0040-4039

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JF - Tetrahedron Letters

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ER -

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

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