190438
(S)-(−)-2-Amino-3-phenyl-1-propanol
98%, optical purity ee: 99% (HPLC)
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L-Phenylalaninol
C6H5CH2CH(NH2)CH2OH
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Quality Level
assay
98%
form
solid
optical activity
[α]22/D −22.8°, c = 1.2 in 1 M HCl
optical purity
ee: 99% (HPLC)
mp
92-94 °C (lit.)
SMILES string
N[C@H](CO)Cc1ccccc1
InChI
1S/C9H13NO/c10-9(7-11)6-8-4-2-1-3-5-8/h1-5,9,11H,6-7,10H2/t9-/m0/s1
InChI key
STVVMTBJNDTZBF-VIFPVBQESA-N
Related Categories
General description
(S)-(-)-2-Amino-3-phenyl-1-propanol is a chiral amino alcohol.
Application
(S)-(-)-2-Amino-3-phenyl-1-propanol can undergo condensation with 5-nitrosalicylaldehyde to form (S)-2-[(1-benzyl-2-hydroxyethylimino)methyl]-4-nitrophenol, a new chiral Schiff base. It reacts with substituted salicylaldehydes to form tridentate chiral Schiff base ligands, which can form H-bonded chiral supramolecular metal-organic architectures. It can also be used in the synthesis of an unnatural tripeptide, which can enhance the antimicrobial activity of methicillin against methicillin resistant Staphylococcus aureus.
Reacts with nitriles to form oxazolines which are useful in Pd-catalyzed allylic substitution. Also employed in amidation for chiral resolution and NADH modeling.
wgk_germany
WGK 3
ppe
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Certificates of Analysis (COA)
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Tetrahedron Letters, 34, 7081-7081 (1993)
Intramolecular hydrogen transfer in (S)-2-[(1-benzyl-2-hydroxyethylimino) methyl]-4-nitrophenol, a new chiral Schiff base.
Acta Crystallographica Section E, Structure Reports Online, 61(11), o3825-o3827 (2005)
Chiral supramolecular metal-organic architectures from dinuclear copper complexes.
Polyhedron, 28(3), 630-636 (2009)
Tetrahedron Letters, 34, 2015-2015 (1993)
Journal of peptide science : an official publication of the European Peptide Society, 11(7), 431-435 (2005-01-07)
2-Oxoamides based on long chain beta-amino acids were synthesized. 1-Benzyl substituted long chain amines, needed for such synthesis, were synthesized starting from Boc-phenylalaninol. The oxidative conversion of a phenyl group to a carboxyl group was used as the key transformation
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