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Merck
CN

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:
20859-02-3
Molecular Weight:
131.17
NACRES:
NA.22
PubChem Substance ID:
24856311
UNSPSC Code:
12352209
MDL number:
MFCD00064218
Beilstein/REAXYS Number:
1721824

Key Documents

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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

200

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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.

General description

L-tert-Leucine is an amino acid used as a precursor for synthesizing chiral tridentate Schiff base ligands.

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCN9731
BCCN8694
BCCL8088
BCCK1130
BCBG8454V

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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)
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)
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)
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)
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