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N-Boc-D-fenilglicina, 99 %, Thermo Scientific Chemicals
N-Boc-D-fenilglicina, 99 %, Thermo Scientific Chemicals
N-Boc-D-fenilglicina, 99 %, Thermo Scientific Chemicals
Thermo Scientific Chemicals

N-Boc-D-fenilglicina, 99 %, Thermo Scientific Chemicals

CAS: 33125-05-2 | C13H17NO4 | 251.28 g/mol
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Cantidad:
1 g
5 g
Número de catálogo L18540.03
también denominado L18540-03
Precio (USD)
-
Cantidad:
1 g
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Identificadores químicos
CAS33125-05-2
IUPAC Name2-{[(tert-butoxy)carbonyl]amino}-2-phenylacetic acid
Molecular FormulaC13H17NO4
InChI KeyHOBFSNNENNQQIU-UHFFFAOYNA-N
SMILESCC(C)(C)OC(=O)NC(C(O)=O)C1=CC=CC=C1
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EspecificacionesSpecification SheetHoja de especificaciones
Optical Rotation-142.9 ± 0.1? (C=1 in ethanol)
Melting Point (clear melt)88.0-95.0?C
FormPowder
Appearance (Color)White
Assay (Aqueous acid-base Titration)≥98.5 to ≤101.5%
It is a reagent of choice for assignment of absolute configuration of chiral primary amines by 1H NMR, giving better results than Mosher's acid ((R)-(+)-Methoxy-(trifluoromethyl)­phenyl­acetic acid. αR)-α-[[(1,1-Dimethylethoxy)carbonyl]amino]-benzeneacetic Acid is D-(+)-2-Phenylglycine with Boc protecting group. (αR)-α-[[(1,1-Dimethylethoxy)carbonyl]amino]-benzeneacetic Acid is used as part of a catalyst combination to catalyze regioselective [4 + 2] cycloadditions of β-substituted cyclic enones and polyconjugated malononitriles. It can also be used to catalyze stereoselective preparation of polyfunctional nitrocyclohexene carboxaldehydes.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
It is a reagent of choice for assignment of absolute configuration of chiral primary amines by 1H NMR, giving better results than Mosher′s acid ((R)-(+)-ɑ-Methoxy-ɑ-(trifluoromethyl)­phenyl­acetic acid. αR)-α-[[(1,1-Dimethylethoxy)carbonyl]amino]-benzeneacetic Acid is D-(+)-2-Phenylglycine with Boc protecting group. (αR)-α-[[(1,1-Dimethylethoxy)carbonyl]amino]-benzeneacetic Acid is used as part of a catalyst combination to catalyze regioselective [4 + 2] cycloadditions of β-substituted cyclic enones and polyconjugated malononitriles. It can also be used to catalyze stereoselective preparation of polyfunctional nitrocyclohexene carboxaldehydes.

Solubility
Insoluble in water. Slightly soluble in DMSO and methanol.

Notes
Store away from oxidizing agents. Keep the container tightly closed and place it in a cool, dry and well ventilated condition.
RUO – Research Use Only

General References:

  1. En Zhang, et al. Organocatalytic Asymmetric Vinylogous α-Ketol Rearrangement: Enantioselective Construction of Chiral All-Carbon Quaternary Stereocenters in Spirocyclic Diketones via Semipinacol-Type 1,2-Carbon Migration.J. Am. Chem. Soc.,2009,131(41), 14626-14627.
  2. AV Rama Rao, et al. A convenient diastereoselective total synthesis of andrimid.Tetrahedron Lett.,1991,32(34), 4393-4396.
  3. Reagent of choice for assignment of absolute configuation of chiral primary amines by 1H NMR, giving better results than Mosher's acid ((R)-(+)-ɑ-Methoxy-ɑ-(trifluoromethyl) phenyl acetic acid, B22968): J. Org. Chem., 64, 4669 (1999).