N-Boc-trans-4-tosyloxy-L-proline methyl ester
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N-Boc-trans-4-tosyloxy-L-proline methyl ester

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A reagent used in the preparation of bicycloazahydantoins as androgen receptor antagonists.

Category
BOC-Amino Acids
Catalog number
BAT-009043
CAS number
88043-21-4
Molecular Formula
C18H25NO7S
Molecular Weight
399.46
N-Boc-trans-4-tosyloxy-L-proline methyl ester
IUPAC Name
1-O-tert-butyl 2-O-methyl (2S,4R)-4-(4-methylphenyl)sulfonyloxypyrrolidine-1,2-dicarboxylate
Synonyms
Boc-trans-4-Tosyloxy-L-proline methyl ester; N-Boc-trans-4-(p-tosyloxy)-L-proline methyl ester; (2S,4R)-1-Tert-Butyl 2-Methyl 4-(Tosyloxy)Pyrrolidine-1,2-Dicarboxylate; Boc-Hyp(Tos)-Ome
Appearance
White Solid
Purity
95%
Density
1.265 g/cm3
Boiling Point
520.5ºC at 760 mmHg
InChI
InChI=1S/C18H25NO7S/c1-12-6-8-14(9-7-12)27(22,23)26-13-10-15(16(20)24-5)19(11-13)17(21)25-18(2,3)4/h6-9,13,15H,10-11H2,1-5H3/t13-,15+/m1/s1
InChI Key
UKVKNGDXVREPDE-HIFRSBDPSA-N
Canonical SMILES
CC1=CC=C(C=C1)S(=O)(=O)OC2CC(N(C2)C(=O)OC(C)(C)C)C(=O)OC
1.α-Terpineol attenuates morphine-induced physical dependence and tolerance in mice: role of nitric oxide.
Parvardeh S1, Moghimi M1, Eslami P2, Masoudi A1. Iran J Basic Med Sci. 2016 Feb;19(2):201-8.
OBJECTIVES: Dependence and tolerance to opioid analgesics are major problems limiting their clinical application. α-Terpineol is a monoterpenoid alcohol with neuroprotective effects which is found in several medicinal plants such as Myrtus communis, Laurus nobilis, and Stachys byzantina. It has been shown that some of these medicinal plants such as S. byzantina attenuate dependence and tolerance to morphine. Since α-terpineol is one of the bioactive phytochemical constituent of these medicinal plants, the present study was conducted to investigate the effects of α-terpineol on morphine-induced dependence and tolerance in mice.
2.Comparison and validation of 2 analytical methods for the determination of free fatty acids in dairy products by gas chromatography with flame ionization detection.
Mannion DT1, Furey A2, Kilcawley KN3. J Dairy Sci. 2016 Apr 13. pii: S0022-0302(16)30178-3. doi: 10.3168/jds.2015-10795. [Epub ahead of print]
Accurate quantification of free fatty acids (FFA) in dairy products is important for quality control, nutritional, antimicrobial, authenticity, legislative, and flavor purposes. In this study, the performance of 2 widely used gas chromatographic flame ionization detection methods for determination of FFA in dairy products differing in lipid content and degree of lipolysis were evaluated. We used a direct on-column approach where the isolated FFA extract was injected directly and a derivatization approach where the FFA were esterified in the injector to methyl esters using tetramethylammonium hydroxide as a catalyst. A comprehensive validation was undertaken to establish method linearity, limits of detection, limits of quantification, accuracy, and precision. Linear calibrations of 3 to 700 mg/L (R2 > 0.999) and 20 to 700 mg/L (R2 > 0.997), and limits of detection and limits of quantification of 0.7 and 3 mg/L and 5 and 20 mg/L were obtained for the direct injection on-column and the derivatization method, respectively.
3.Diagnostic Ultrasound High Mechanical Index Impulses Restore Microvascular Flow in Peripheral Arterial Thromboembolism.
Porter TR1, Radio S2, Lof J2, Everbach C3, Powers JE4, Vignon F5, Shi WT5, Xie F2. Ultrasound Med Biol. 2016 Apr 12. pii: S0301-5629(16)00062-4. doi: 10.1016/j.ultrasmedbio.2016.02.001. [Epub ahead of print]
We sought to explore mechanistically how intermittent high-mechanical-index (MI) diagnostic ultrasound impulses restore microvascular flow. Thrombotic microvascular obstruction was created in the rat hindlimb muscle of 36 rats. A diagnostic transducer confirmed occlusion with low-MI imaging during an intravenous microbubble infusion. This same transducer was used to intermittently apply ultrasound with an MI that produced stable or inertial cavitation (IC) for 10 min through a tissue-mimicking phantom. A nitric oxide inhibitor, L-Nω-nitroarginine methyl ester (L-NAME), was pre-administered to six rats. Plateau microvascular contrast intensity quantified skeletal microvascular blood volume, and postmortem staining was used to detect perivascular hemorrhage. Intermittent IC impulses produced the greatest recovery of microvascular blood volume (p < 0.0001, analysis of variance). Nitric oxide inhibition did not affect the skeletal microvascular blood volume improvement, but did result in more perivascular hemorrhage.
4.The synthesis and investigation of impurities found in Clandestine Laboratories: Baeyer-Villiger Route Part I; Synthesis of P2P from benzaldehyde and methyl ethyl ketone.
Doughty D1, Painter B1, Pigou PE1, Johnston MR2. Forensic Sci Int. 2016 Mar 24;263:55-66. doi: 10.1016/j.forsciint.2016.03.034. [Epub ahead of print]
The synthesis of impurities detected in clandestinely manufactured Amphetamine Type Stimulants (ATS) has emerged as more desirable than simple "fingerprint" profiling. We have been investigating the impurities formed when phenyl-2-propanone (P2P) 5, a key ATS precursor, is synthesised in three steps; an aldol condensation of benzaldehyde and methyl ethyl ketone (MEK); a Baeyer-Villiger reaction; and ester hydrolysis. We have identified and selectively synthesised several impurities that may be used as route specific markers for this series of synthetic steps. Specifically these impurities are 3-methyl-4-phenyl-3-buten-2-one 3, 2-methyl-1,5-diphenylpenta-1,4-diene-3-one 9, 2-(methylamino)-3-methyl-4-phenyl-3-butene 16, 2-(Methylamino)-3-methyl-4-phenylbutane 17, and 1-(methylamino)-2-methyl-1,5-diphenylpenta-4-ene-3-one 22.
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