269107
L-tert-Leucine
99%, for peptide synthesis
Synonym(s):
(S)-2-Amino-3,3-dimethylbutyric acid, L-α-tert-Butylglycine
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About This Item
Linear Formula:
(CH3)3CCH(NH2)CO2H
CAS Number:
Molecular Weight:
131.17
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352209
MDL number:
Beilstein/REAXYS Number:
1721824
Product Name
L-tert-Leucine, 99%
InChI
1S/C6H13NO2/c1-6(2,3)4(7)5(8)9/h4H,7H2,1-3H3,(H,8,9)/t4-/m1/s1
SMILES string
CC(C)(C)[C@H](N)C(O)=O
InChI key
NPDBDJFLKKQMCM-SCSAIBSYSA-N
assay
99%
form
powder
optical activity
[α]20/D −9.5°, c = 3 in H2O
optical purity
ee: 99% (GLC)
reaction suitability
reaction type: solution phase peptide synthesis
mp
≥300 °C (lit.)
application(s)
peptide synthesis
Quality Level
General description
L-tert-Leucine is an amino acid used as a precursor for synthesizing chiral tridentate Schiff base ligands.
Application
L-tert-Leucine can be used:
- As a key precursor in the synthesis of a chiral phosphinooxazoline ligand, (S)-tert-butylPHOX.
- In the synthesis of chiral copper(II) polymers that can catalyze the kinetic resolution of secondary alcohols by acylation.
- In metal-free tandem radical cyclization reactions to synthesize 6-alkyl/acyl phenanthridines.
- In the preparation of tert-leucine-derived N-acetylthiazolidinethione auxiliary that provides high levels of diastereoselection in acetate aldol reactions with a variety of aldehydes.
Storage Class
11 - Combustible Solids
wgk
WGK 1
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Synthesis, structure and application of chiral copper (II) coordination polymers for asymmetric acylation.
Jammi S, et al.
Inorganic Chemistry, 47(12), 5093-5098 (2008)
Highly Selective Asymmetric Acetate Aldol Reactions of an N-Acetyl Thiazolidinethione Reagent.
Zhang Y, et al.
Organic Letters, 6(1), 23-25 (2004)
Tridentate ligands derived from L-tert-Leucine for the Cu (II) mediated asymmetric Henry reaction
Korkmaz N, et al.
Turkish Journal of Chemistry, 35, 361-374 (2011)
Use of unprotected amino acids in metal-free tandem radical cyclization reactions: divergent synthesis of 6-alkyl/acyl phenanthridines.
Lu S C, et al.
Royal Society of Chemistry Advances, 7(88), 55891-55896 (2017)
Preparation of (S)?tert?Butyl PHOX: (Oxazole, 4?(1, 1?Dimethylethyl)?2?[2?(Diphenylphosphino) Phenyl]?4, 5?Dihydro?(4S)?).
Krout M R, et al.
Organic Syntheses, 86, 181-193 (2003)
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