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33125-05-2 - N-Boc-D-phenylglycine, 99% - Boc-D-Phg-OH - N-(tert-Butoxycarbonyl)-D-phenylglycine - L18540 - Alfa Aesar

L18540 N-Boc-D-phenylglycine, 99%

CAS Number
33125-05-2
Synonyms
Boc-D-Phg-OH
N-(tert-Butoxycarbonyl)-D-phenylglycine

Size Price ($) Quantity Availability
1g 33.44
5g 131.84
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N-Boc-D-phenylglycine, 99%

MDL
MFCD00062043

Chemical Properties

Formula
C13H17NO4
Formula Weight
251.28
Melting point
90-92°
Solubility
Insoluble in water. Slightly soluble in DMSO and methanol.

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)-(+)-?-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.

Notes

Store away from oxidizing agents. Keep the container tightly closed and place it in a cool, dry and well ventilated condition.

Literature References

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.

AV Rama Rao, et al. A convenient diastereoselective total synthesis of andrimid.Tetrahedron Lett.,1991,32(34), 4393-4396.

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)­phenyl­acetic acid, B22968): J. Org. Chem., 64, 4669 (1999).

Other References

Beilstein
3033982
Harmonized Tariff Code
2924.29
TSCA
No

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