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269107

Sigma-Aldrich

L-tert-Leucine

99%, for peptide synthesis

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Synonym(s):
(S)-2-Amino-3,3-dimethylbutyric acid, L-α-tert-Butylglycine
Linear Formula:
(CH3)3CCH(NH2)CO2H
CAS Number:
20859-02-3
Molecular Weight:
131.17
Beilstein:
1721824
MDL number:
MFCD00064218
UNSPSC Code:
12352209
PubChem Substance ID:
24856311
NACRES:
NA.22

Quality Level

200

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

SMILES string

CC(C)(C)[C@H](N)C(O)=O

InChI

1S/C6H13NO2/c1-6(2,3)4(7)5(8)9/h4H,7H2,1-3H3,(H,8,9)/t4-/m1/s1

InChI key

NPDBDJFLKKQMCM-SCSAIBSYSA-N

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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.

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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