26782-71-8

Basic information

• Product Name: D-tert-Butylglycine
• Synonyms: D-ALPHA-T-BUTYL-GLY-OH;D-ALPHA-TERT-BUTYLGLYCINE;(R)-2-AMINO-3,3-DIMETHYLBUTYRIC ACID;(R)-TERT-LEUCINE;TBU-D-GLYCINE;(R)-2-Amino-3,3-dimethylbutyric acid~D-2-tert-Butylglycine~H-D-Tle-OH;D-a-t-Butylglycine;D-TERT-LEUCINE, 99% (99% EE/GLC)
• CAS NO: 26782-71-8
• Molecular Formula: C₆H₁₃NO₂
• Molecular Weight: 131.17
• EINECS: 1308068-626-2
• Product Categories: Amino acids, non natural;Chiral Compounds;Amino Acids;Leucine [Leu, L];Peptide
• Mol File: 26782-71-8.mol
• Article Data: 20

Chemical Properties

• Melting Point: ≥300 °C(lit.)
• Boiling Point: 217.7 °C at 760 mmHg
• Flash Point: 85.5 °C
• Appearance: White crystalline powder
• Density: 1.038 g/cm³
• Vapor Pressure: 0.0499mmHg at 25°C
• Refractive Index: 9 ° (C=3, H2O)
• Storage Temp.: Store at RT.
• PKA: 2.39±0.12(Predicted)
• Water Solubility: Soluble in water.
• BRN: 1721825
• CAS DataBase Reference: D-tert-Butylglycine(CAS DataBase Reference)
• NIST Chemistry Reference: D-tert-Butylglycine(26782-71-8)
• EPA Substance Registry System: D-tert-Butylglycine(26782-71-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• Hazardous Substances Data: 26782-71-8(Hazardous Substances Data)

Usage

Chemical Properties

White crystalline powder

Uses

D-tert-Leucine is used for synthesis of amino acids e.g. in the synthesis of aldehydes by double alkylation of unsaturated aldimines of tert-Leu esters.

InChI:InChI=1/C6H13NO2/c1-6(2,3)4(7)5(8)9/h4H,7H2,1-3H3,(H,8,9)/t4-/m0/s1

Upstream product

• 62965-57-5 (±)-2-amino-3,3-dimethylbutanamide 
• 33105-81-6 2-amino-3,3-dimethylbutanoic acid 
• 124655-17-0 (R)-2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoic acid 
• 22146-58-3 (+/-)-2-acetylamino-3,3-dimethylbutyric acid 
• 20429-42-9 (E)-3,3-dimethyl-1-nitrobut-1-ene 
• 630-19-3 pivalaldehyde 
• 10049-60-2 sec-butylamine hydrochloride 
• 815-17-8 trimethylpyruvic acid 
• 17026-42-5 O,O'-dibenzoyl-D-tartaric acid 
• 1355742-77-6 (R)-2-benzyloxycarbonylamino-3,3-dimethylbutanenitrile 
• 68222-59-3 2(S)-{(benzyloxycarbonyl)amino}-3,3-dimethylbutanoic acid 
• 62965-34-8 Trimethylpyruvic acid oxime 
• 92571-58-9 DL-2-formylamino-3,3-dimethyl-butyric acid 
• 75-97-8 3,3-dimethyl-butan-2-one 

Downstream Products

• 214353-45-4 N-[4-(4-chlorophenoxy)benzenesulfonyl]-D-tert-leucine 
• 1314036-63-9 (S)-N¹,N¹-diethyl-3,3-dimethylbutane-1,2-diamine 
• 1310695-61-4 N-[(2R)-1-{(2S)-2-[5-(4’-{2-[(2S)-1-{(2R)-2-[(cyclopropylcarbonyl)amino]-3,3-dimethylbuttanoyl}pyrrolidin-2-yl]-1,3-thiazol-5-yl}biphenyl-4-yl)-1,3-thiazol-2-yl]pyrrolidin-1-yl}-3,3-dimethyl-1-oxobutan-2-yl]cyclopropanecarboxamide 
• 952596-16-6 N-(3-methoxyphenylsulfonyl)-D-tert-leucine 
• 3907-02-6 (2R)-2-amino-3,3-dimethylbutan-1-ol 
• 132684-60-7 L-2-amino-3,3-dimethylbutyric acid 
• 167223-43-0 L-tert-butylglycine methyl ester hydrochloride 
• 218800-31-8 (R)-2-amino-3,3-dimethyl-1,1-diphenylbutan-1-ol 
• 26547-87-5 (R)-2-bromo-3,3-dimethyl-butyric acid 
• 1313705-92-8 tert-butyl (R)-4-(tert-butyl)-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide 
• 164858-79-1 (R)-4-(tert-butyl)-2-(2-(diphenylphosphino)phenyl)-4,5-dihydrooxazole 

Relevant articles and documents

An efficient and selective enzymatic oxidation system for the synthesis of enantiomerically pure D-tert-Leucine

(Matrix presented) D-tert-Leucine was prepared with an enantiomeric excess of >99% by an enzyme-catalyzed oxidative resolution of the racemic mixture of DL-tert-leucine with use of leucine dehydrogenase. The L-amino acid was oxidized completely due to coupling of the primary reaction with a highly efficient irreversible NAD+-regenerating step by NADH oxidase.

Method for preparing D-type or L-type tert-leucine

The invention discloses a method for preparing D-type or L-type tert-leucine, and belongs to the technical field of organic synthesis. The method comprises the following steps: 1, condensing glyoxylate serving as a raw material with chiral tert-butyl sulfinamide to obtain Schiff base; and 2, carrying out a reaction on the Schiff base with a tert-butyl Grignard reagent and a catalyst under a low-temperature condition, and hydrolyzing the reaction product under an acid/alkali condition to obtain D-type or L-type tert-leucine. The method is simple and convenient to operate and high in reaction yield, the purity and content of the obtained product are greater than 99%, the content of a single impurity is less than 0.2%, the chiral purity is greater than or equal to 98.5%, and the method has apotential process amplification prospect.

Sequential ruthenium catalysis for olefin isomerization and oxidation: Application to the synthesis of unusual amino acids

How can you use a ruthenium isomerization catalyst twice? A ruthenium-catalyzed sequence for the formal two-carbon scission of allyl groups to carboxylic acids has been developed. The reaction includes an initial isomerization step using commercially available ruthenium catalysts followed by in situ transformation of the complex to a metal-oxo species, which is capable of catalyzing subsequent oxidation reactions. The method enables enantioselective syntheses of challenging α-tri- and tetrasubstituted α-amino acids including an expedient total synthesis of the antiepileptic drug levetiracetam.