Boc-(2R,5S)-5-phenylpyrrolidine-2-carboxylic acid - CAS 158706-46-8

Category
BOC-Amino Acids
Catalog number
BAT-007911
CAS number
158706-46-8
Molecular Formula
C16H21NO4
Molecular Weight
291.34
Boc-(2R,5S)-5-phenylpyrrolidine-2-carboxylic acid
Synonyms
(2R,5S)-1-(tert-Butoxycarbonyl)-5-phenylpyrrolidine-2-carboxylic acid; (2r,5s)-boc-5-phenyl-pyrrolidine-2-carboxylic acid; (5S)-1-(tert-Butoxycarbonyl)-5-phenyl-D-proline; (2R,5S)-1-[(2-methylpropan-2-yl)oxycarbonyl]-5-phenylpyrrolidine-2-carboxylic acid
Appearance
White powder
Purity
≥ 99% (HPLC)
Density
1.196±0.06 g/cm3 (Predicted)
Boiling Point
441.5±45.0 °C (Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C16H21NO4/c1-16(2,3)21-15(20)17-12(9-10-13(17)14(18)19)11-7-5-4-6-8-11/h4-8,12-13H,9-10H2,1-3H3,(H,18,19)/t12-,13+/m0/s1
InChI Key
ADTXMICUZGOWDF-QWHCGFSZSA-N
Canonical SMILES
CC(C)(C)OC(=O)N1C(CCC1C(=O)O)C2=CC=CC=C2
1.Iminolactones as tools for inversion of the absolute configuration of α-amino acids and as inhibitors of cancer cell proliferation.
Jensen CM1, Chow HQ1, Chen M2, Zhai L1, Frydenvang K1, Liu H1, Franzyk H1, Christensen SB3. Eur J Med Chem. 2016 May 23;114:118-33. doi: 10.1016/j.ejmech.2016.02.037. Epub 2016 Feb 23.
A library of iminolactones was prepared by esterification of several 2-hydroxyketones with a number of N-protected d- and l-α-amino acids. Some of the hydroxyketones were of terpenoid origin while others were obtained via synthesis. After N-deprotection of the intermediate esters, the free amines spontaneously underwent condensation with the ketone to form iminolactones. Esters of (1S,2S,5S)-2-hydroxypinan-3-one with both d- and l-α-amino acids were partially epimerized at the α-carbon atom to give a diastereomeric ester mixture. Only iminolactones of l-amino acids were formed after cyclization of (1S,2S,5S)-2-hydroxypinan-3-one, and correspondingly only d-amino acid iminolactones were formed after reaction with (1R,2R,5R)-2-hydroxypinan-3-one. The protocol thus enables inversion of the absolute configuration of amino acids. Some members of the prepared library of iminolactones displayed significant anti-proliferative effects toward three cancer cell lines (EL4, MCF7, PC3) with insignificant effect on non-malign cell lines (McCoy, MCF10A, NIH3T3).
2.[Stereoselective synthesis of polyhydroxylated amines using (S)-pyroglutamic acid derivatives].
Ikota N1. Yakugaku Zasshi. 2014;134(1):77-88.
Naturally occurring polyhydroxylated amines such as (+)-1-deoxynojirimycin, polyoxamic acid, anisomycin, (-)swainsonine, and alexine stereoisomers, which have interesting biological activities including glucosidase- and mannosidase-inhibitory activity, immunoregulatory activity, and antibacterial effects, were synthesized stereoselectively starting from (S)-pyroglutamic acid derivatives. α,β-Unsaturated lactams ((S)-5-hydroxymethyl-2-oxo-3-pyrroline derivatives), α,β-unsaturated δ-lactone ((S)-4-amino-2-penten-5-olide derivative), and E-olefin ((S,E)-methyl-4-amino-5-hydroxypent-2-enoate derivative) from (S)-pyroglutamic acid derivatives were dihydroxylated using OsO4 in the presence of N-methyl morpholine N-oxide (NMO) to afford various chiral building blocks with different configurations. The stereoselectivity of cis-dihydroxylation for α,β-unsaturated lactams and α,β-unsaturated δ-lactone was very high, while the stereoselectivity was low for E-olefin.
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