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

Tetrahedron Letters

Volumn 51, Issue 41, 2010, Pages 5361-5363

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

^a Obiter Research   (United States)

^b UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^c Radius Health Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 3 BENZYLOXY 4,4,4 TRIFLUOROBUTANOIC ACID; ALDEHYDE; AMINO ACID DERIVATIVE; ANDROGEN; ANDROGEN RECEPTOR; SELECTIVE ANDROGEN RECEPTOR MODULATOR; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; BINDING AFFINITY; CHEMICAL STRUCTURE; CONTROLLED STUDY; DEPROTECTION REACTION; DIASTEREOISOMER; NONHUMAN; RAT; STEREOCHEMISTRY; SYNTHESIS;

TRIFLUORO;

EID: 77956619036     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.07.147     Document Type: Article

References (14)

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11. The Herschberger assay looks primarily at the ability of androgens to increase muscle size in an immature, castrated rat. In addition, androgenic effects are looked at primarily by weighing the prostate. Selective compounds will show a greater increase in the levator ani relative to the prostate when compared to testosterone treated, castrated animals or to intact animals that have not been treated. Immature Sprague Dawley male rats were obtained Charles River Laboratories (Stoneridge, NY). All animals were maintained in a temperature and humidity controlled room with a 12 h light: 12 h dark cycle, with ad lib access to food (TD 291615, Teklad, Madison, WI) and water. Rats were anesthetized and orchidectomized (GDX) or sham surgery (SHAM) was performed. After a 7-day recovery period, the animals were randomized according to weight and assigned to treatment groups (n = 5), SHAM, OVX + vehicle, OVX + compd treated. Testosterone propionate (TP 1 mg/kg in 5% DMSO/95% corn oil) was administered by once daily subcutaneous injections, while the compound was dosed in vehicle (0.5% carboxymethylcellulose) and administered by once daily oral gavage. The rats were then dosed once daily for 4 days. All animals were euthanized via carbon dioxide inhalation 24 h after the last dose. The prostate and levator ani and bulbocavernosus (LABC) tissues were removed, weighed and recorded.
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