26782-71-8

Usage

Uses

Used in Pharmaceutical Industry:
D-tert-Butylglycine is used as a chiral building block for the synthesis of various pharmaceutical compounds. Its unique chemical properties make it a valuable component in the development of new drugs and therapeutic agents.
Used in Chemical Industry:
D-tert-Butylglycine is used as a key intermediate in the synthesis of amino acids, such as in the synthesis of aldehydes by double alkylation of unsaturated aldimines of tert-Leu esters. This versatile compound plays a crucial role in the production of various organic compounds and specialty chemicals.

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

• 92571-59-0 D-2-formylamino-3,3-dimethyl-butyric acid 
• 70874-05-4 Z-D-Tle 
• 112245-08-6 methyl (R)-2-amino-3,3-dimethylbutanoate 
• 253178-21-1 ethyl (R)-2-amino-3,3-dimethylbutanoate 
• 38559-30-7 3,3-dimethyl-2-oxo-butanoic acid phenyhydrazone 
• 119825-41-1 (R)-2-Amino-N-tert-butyl-3,3-dimethyl-butyramide; hydrochloride 
• 112022-93-2 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-2-[((R)-1-tert-butylcarbamoyl-2,2-dimethyl-propyl)-formyl-amino]-4,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 206068-51-1 (R)-3,3-Dimethyl-2-((R)-2-oxo-4-phenyl-oxazolidin-3-yl)-butyric acid 
• 380380-13-2 D-2-acetylamino-3,3-dimethylbutyric acid 2-chloroethyl ester 
• 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 
• 153960-35-1 N-Boc-D-tert-leucine methyl ester 
• 20429-42-9 (E)-3,3-dimethyl-1-nitrobut-1-ene 

Downstream Products

• 26547-87-5 (R)-2-bromo-3,3-dimethyl-butyric acid 
• 218800-31-8 (R)-2-amino-3,3-dimethyl-1,1-diphenylbutan-1-ol 
• 167223-43-0 L-tert-butylglycine methyl ester hydrochloride 
• 214353-45-4 N-[4-(4-chlorophenoxy)benzenesulfonyl]-D-tert-leucine 
• 124655-17-0 (R)-2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoic acid 
• 1215067-69-8 C₁₃H₁₇NO₃ 
• 1215067-70-1 C₁₉H₂₅NO₄ 
• 1258066-72-6 (R)-2-((1-(tert-butoxycarbonyl)-3-(methoxycarbonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)methylamino)-3,3-dimethylbutanoic acid 
• 268556-62-3 (R)-N-benzyl 2-amino-3,3-dimethylbutanamide 

Relevant academic research and scientific papers

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.

Simultaneous Preparation of (S)-2-Aminobutane and d -Alanine or d -Homoalanine via Biocatalytic Transamination at High Substrate Concentration

(S)-2-Aminobutane, d-alanine, and d-homoalanine are important intermediates for the production of various active pharmaceutical ingredients and food additives. The preparation of these small chiral amine or amino acids with high water solubility still demands searching for efficient methods. In this work, we identified an ω-transaminase (ω-TA) from Sinirhodobacter hungdaonensis (ShdTA) that catalyzed the kinetic resolution of racemic 2-aminobutane at a concentration of 800 mM using pyruvate as the amino acceptor, leading to the simultaneous isolation of enantiopure (S)-2-aminobutane and d-alanine in 46% and 90% yield, respectively. In addition, (S)-2-aminobutane (98% ee) and d-homoalanine (99% ee) were isolated in 45% and 93% yield, respectively, in the kinetic resolution of racemic 2-aminobutane at a concentration of 400 mM coupled with deamination of l-threonine by threonine deaminase. We thus developed a biocatalytic process for the practical synthesis of these valuable small chiral amine and d-amino acids.

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.

Structure-guided engineering of: Meso -diaminopimelate dehydrogenase for enantioselective reductive amination of sterically bulky 2-keto acids

meso-Diaminopimelate dehydrogenase (DAPDH) and mutant enzymes are an excellent choice of biocatalysts for the conversion of 2-keto acids to the corresponding d-amino acids. However, their application in the enantioselective reductive amination of bulky 2-keto acids, such as phenylglyoxylic acid, 2-oxo-4-phenylbutyric acid, and indole-3-pyruvic acid, is still challenging. In this study, the structure-guided site-saturation mutagenesis of a Symbiobacterium thermophilum DAPDH (StDAPDH) gave rise to a double-site mutant W121L/H227I, which showed dramatically improved enzyme activities towards various 2-keto acids including these sterically bulky substrates. Several d-amino acids were prepared in optically pure form. The molecular docking of substrates into the active sites of wild-type and mutant W121L/H227I enzymes revealed that the substrate binding cavity of the mutant enzyme was reshaped to accommodate these bulky substrates, thus leading to higher enzyme activity. These results lay a foundation for further shaping the substrate binding pocket and manipulating the interactions between the substrate and binding sites to access highly active d-amino acid dehydrogenases for the preparation of synthetically challenging d-amino acids.

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.

Preparation D at the same time-and L- uncle leucine method (by machine translation)

This invention relates to a kind of simultaneously preparing D-and L- uncle leucine method, comprising the following steps: step (1): the positive butanol and 1,1-dichloroethylene reaction, to obtain 3,3-dimethyl butanoic acid product; step (2): in the 3,3-dimethyl-butyric acid, a catalyst is added in the product, at the same time access air and chlorine, to chloropivaloyl, to obtain 2-chloro -3,3-dimethyl butanoic acid; step (3): the obtained 2-chloro -3,3-dimethyl butanoic acid for aminolysis reaction, to obtain D-, L-tert-leucine; step (4): the D-, L-tert-leucine for acetylation and acetyl chloride, with L-heat-stable to amino acid acylase split and other processing, respectively obtained L-tert-leucine and D-tert-leucine; step (5): the split recovery acetylation or chloroactic acidylated recovery D-tert-leucine for racemic, is circulated and split. The present invention uses low-cost normal butanol and 1,1-dichloroethylene as the starting material. From economic benefits speaking, the cost of this invention is substantially below that of the biological reduction method. (by machine translation)

A process for the preparation of enantiomerically pure tert-leucine

A Process for the Preparation of Enantiomerically Pure tert-Leucine : Enantiomerically pure L-tert-leucine and D-tert-leucine were prepared from (DL)-tert-leucine by diastereomeric salt formation using dibenzoyl-d-tartaric acid as the resolving agent.

PROCESS FOR THE PREPARATION OF ENANTIOMERICALLY PURE tert-LEUCINE

Enantiomerically pure L-tert-leucine and D-tert-leucine were prepared from (DL)-tert-leucine by diastereomeric salt formation using dibenzoyl-d-tartaric acid as the resolving agent.

Enantioselective hydrocyanation of N-protected aldimines

Enantioselective hydrocyanation of N-benzyloxycarbonyl aldimines catalyzed by a Ru[(S)-phgly]2[(S)-binap]/C6H5OLi system or a bimetallic complex [Li{Ru[(S)-phgly]2[(S)-binap]}]Cl affords the amino nitriles in 92 - 99% ee. The reaction is carried out in tert-C 4H9OCH3 with a substrate-to-catalyst molar ratio in the range of 500 - 5000 at -20 to 0°C. Primary, secondary, and tertiary alkyl imines as well as the aryl and heteroaryl substrates are smoothly cyanated to produce the desired products in high yield.

Enzymatic approach to both enantiomers of N-Boc hydrophobic amino acids

Protease catalysed hydrolysis of N-Boc-amino acid esters allows us to obtain N-Boc l-acids and d-esters of amino butanoic acid, nor-leucine, nor-valine, leucine and t-leucine in excellent ee. The reaction occurs in short reaction times and high concentrations. When a biphasic system (buffer-MTBE) is employed, a strong solvent effect is observed. This method could be of significance for the preparation of d-t-leucine, for which a practical method is currently unavailable.