96886-55-4

Usage

Uses

It is used in organic synthesis and as an pharmaceutical intermediate.

InChI:InChI=1/C6H11NO2/c1-3-4-6(2,7)5(8)9/h3H,1,4,7H2,2H3,(H,8,9)/t6-/m0/s1

Upstream product

• 191284-36-3 (3S,6R)-3-Allyl-6-isopropyl-3-methyl-5-phenyl-3,6-dihydro-2H-1,4-oxazin-2-one 
• 126402-81-1 isopropyl 2-[(E)-1-phenylmethylideneamino]propanoate 
• 106-95-6 allyl bromide 
• 144125-67-7 C^α-methyl-D,L-allylglycinamide 
• 53933-42-9 2-(benzylidene-amino)-propionic acid methyl ester 
• 91292-73-8 methyl alanine p-chlorobenzaldimine 
• 53777-94-9 C₁₃H₁₃NO₂ 
• 886466-65-5 5-allyloxycarbonyloxy-4-methyl-2-phenyloxazole 
• 1443008-01-2 (S)-2-amino-N-((1S,2S)-2-hydroxy-1,2-diphenylethyl)-N,2-dimethylpent-4-enamide 
• 1443008-27-2 C₂₆H₃₄N₂O₂ 
• 1318776-55-4 R-(-)-benzyl 2-carbamyl-2-methylpent-4-enoate 
• 1266681-06-4 (3S,5aR,6aS,7aS)-3-allyl-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethylbicyclo[4.1.0]hept-1⁽⁶⁾eno[3,4-b][1,4]oxazin-2(3H)-one 
• 56-41-7 L-alanin 
• 898823-65-9 (1S,2R,5S,8R)-5-allyl-5,8,11,11-tetramethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]undec-6-en-4-one 

Downstream Products

• 136707-27-2 N-tert-butyloxycarbonyl-C^α-methyl-L-allylglycine 
• 188194-97-0 (S)-2-[Allyl-(4-methoxy-benzyl)-amino]-2-methyl-pent-4-enoic acid methyl ester 
• 188194-98-1 (S)-2-[Acryloyl-(4-methoxy-benzyl)-amino]-2-methyl-pent-4-enoic acid methyl ester 
• 288617-71-0 (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpent-4-enoic acid 
• 160281-24-3 N--(S)-α-<(2-propenyl)alanyl>>-(R)-alanine methyl ester 
• 797784-94-2 C₁₈H₂₃NO₆ 
• 797784-93-1 (S)-2-benzyloxycarbonylamino-2-methyl-4-pentenoic acid methyl ester 
• 225656-35-9 methyl (S)-2-methyl-2-(toluenesulfonylamino)-4-pentenoate 
• 944086-92-4 (S)-benzyl 2-t-butyloxycarbonylamino-2-methyl-4-pentenoate 
• 88820-87-5 (S)-2-Amino-2-(2-propenyl)propionsaeure-methylester 

Relevant academic research and scientific papers

Asymmetric synthesis of α-amino acids via chiral N-alkylidenesulfinamides

(SR)-(-)-N-[1-(Triethoxymethyl)ethylidene]-p-toluenesulfonamide (2) was synthesized from the addition reaction of triethoxyacetonitrile with MeLi followed by (+)-(R)-d-menthyl-p-toluenesulfinate (1R). Sulfinimine 2 underwent complete stereoselective reduc

Palladium-catalyzed asymmetric decarboxylative allylation of azlactone enol carbonates: Fast access to enantioenriched α-allyl quaternary amino acids

We report a fast protocol for the synthesis of enantioenriched quaternary 4-allyl oxazol-5-ones. The key step is a Pd-catalyzed enantioselective Tsuji allylation of azlactone allyl enol carbonates, which can be easily prepared starting from racemic α-amino acids. The use of (R,R)-DACH-phenyl Trost chiral ligand allowed the attainment of the allylated derivatives in very good yields (83–98 %) and with ee up to 85 %. Scaling up the allylation protocol to gram quantities did not affect the yields end ee values. The produced 4-allyl azlactones can be converted into the corresponding quaternary amino acids or submitted to further synthetic elaborations exploiting the allyl moiety as a handle for the attachment of alkyl and aryl groups. After hydrolysis of the azlactone ring, the zwitterionic amino acids can be attained in enantiopure or nearly optically pure form through only one recrystallization step.

High-chirality method for selectively synthesizing alpha-disubstituted alpha-amino acid

The invention discloses a high-chirality method for selectively synthesizing alpha-disubstituted alpha-amino acid. The high-chirality method for selectively synthesizing alpha-disubstituted alpha-amino acid is characterized by comprising the following steps: step one, reacting S-tert-butanesulfinyl amide or R-tert-butanesulfinyl amide, R-beta substituted ethyl pyruvate and tetraethyl titanate in atetrahydrofuran solvent to obtain a compound C; step two, reacting the compound C with alkyl substituted magnesium bromide under the catalyzing effect of zinc dimethyl in tetrahydrofuran to obtain acompound E; step three, reacting the compound E under the effect of ammonium chloride and anhydrous hydrogen chloride to obtain a compound F; and step four, hydrolyzing the compound F in an ethanol aqueous solution of sodium hydroxide to obtain hydrochloride of a compound G, and carrying out ion exchange to obtain the compound G. The chiral selective reaction is greatly improved, and the method issimple in process, uses cheap and easily obtained raw materials, is simple and convenient to operate, is quite suitable for industrial mass production, and has quite extensive industrial applicationprospect and market value.

METHOD FOR SYNTHESIZING OPTICALLY ACTIVE a-AMINO ACID USING CHIRAL METAL COMPLEX COMPRISING AXIALLY CHIRAL N-(2-ACYLARYL)-2-[5,7-DIHYDRO-6H-DIBENZO[c,e]AZEPIN-6-YL] ACETAMIDE COMPOUND AND AMINO ACID

Objects of the present invention are to provide an industrially applicable method for producing an optically active α-amino acid in high yield and in a highly enantioselective manner, to provide a simple production method of an optically active α,α-disubstituted α-amino acid, and to provide an intermediate useful for the above production methods of an optically active α-amino acid and an optically active α,α-disubstituted α-amino acid. The present invention provides a production method of an optically active α-amino acid or a salt thereof, the production method comprising introducing a substituent into the α carbon in the α-amino acid moiety of a metal complex represented by the following Formula (1): by an alkylation reaction, an aldol reaction, the Michael reaction, or the Mannich reaction, and releasing an optically pure α-amino acid enantiomer or a salt thereof by acid decomposition of the metal complex.

METHOD FOR SYNTHESIZING OPTICALLY ACTIVE α-AMINO ACID USING CHIRAL METAL COMPLEX COMPRISING AXIALLY CHIRAL N-(2-ACYLARYL)-2-[5,7-DIHYDRO-6H-DIBENZO[c,e]AZEPIN-6-YL]ACETAMIDE COMPOUND AND AMINO ACID

Objects of the present invention are to provide an industrially applicable method for producing an optically active ±-amino acid in high yield and in a highly enantioselective manner, to provide a simple production method of an optically active ±,±-disubstituted ±-amino acid, and to provide an intermediate useful for the above production methods of an optically active ±-amino acid and an optically active ±,±-disubstituted ±-amino acid. The present invention provides a production method of an optically active ±-amino acid or a salt thereof, the production method comprising introducing a substituent into the ± carbon in the ±-amino acid moiety of a metal complex represented by the following Formula (1): by an alkylation reaction, an aldol reaction, the Michael reaction, or the Mannich reaction, and releasing an optically pure ±-amino acid enantiomer or a salt thereof by acid decomposition of the metal complex.

Influence of α-methylation in constructing stapled peptides with olefin metathesis

Ring-closing metathesis is commonly utilized in peptide macro-cyclization. The influence of α-methylation of the amino acids bearing the olefin moieties has never been systematically studied. In this report, controlled reactions unambiguously indicate that α-methylation at the N-terminus of the metathesis sites is crucial for this reaction to occur. Also, we first elucidated that the E-isomers of stapled peptides are significantly more helical than the Z-isomers.

Synthesis of quaternary α-methyl α-amino acids by asymmetric alkylation of pseudoephenamine alaninamide pivaldimine

The utility of pseudoephenamine as a chiral auxiliary for the alkylative construction of quaternary α-methyl α-amino acids is demonstrated. The method is notable for the high diastereoselectivities of the alkylation reactions, for its versatility with respect to electrophilic substrate partners, and for its mild hydrolysis conditions, which provide α-amino acids without salt contaminants. Alternatively, α-amino esters can be obtained by direct alcoholysis.

Microbial whole cell-catalyzed desymmetrization of prochiral malonamides: Practical synthesis of enantioenriched functionalized carbamoylacetates and their application in the preparation of unusual α-amino acids

Catalyzed by Rhodococcus erythropolis AJ270, an amidase-containing microbial whole cell catalyst, under very mild conditions, a number of functionalized prochiral malonamides underwent enantioselective desymmetrization reaction to afford high yield of car

Asymmetric synthesis of α-methyl-α-amino acids via diastereoselective alkylation of (1s)-(+)-3-carene derived tricyclic iminolactone

A novel carene-based alanine-equivalent tricyclic iminolactone 16 has been synthesized via stereoselective dihydroxylation of the double bond, IBX oxidation of the secondary alcohol, esterification of the tertiary alcohol, deprotection of the resulting ester, and subsequent cyclization from commercially available (1S)-(+)-3-carene in 79% overall yield. The iminolactone 16 demonstrated high reactivity toward alkylation with a wide range of electrophiles at room temperature under phasetransfer catalysis conditions. The alkylated products were produced with excellent diastereoselectivities (>98% de) in good isolated yields (86-94%). High yields (83-91%) of optically pure (S)-R-methyl-R-substituted-R-amino acids were obtained by basic hydrolysis of the dialkylated iminolactones with the recovery of the chiral auxiliary 15 (78-87%).

Rapid asymmetric synthesis of amino acids via NiII complexes based on new fluorine containing chiral auxiliaries

New fluorine-containing chiral auxiliaries (S)-N-(2-benzoylphenyl)-1-(2- fluorobenzyl)-, (S)-N-(2-benzoylphenyl)-1-(3-fluorobenzyl)-, and (S)-N-(2-benzoylphenyl)-1-(4-fluorobenzyl)-pyrrolidine-2-carboxamide and their NiII complexes of Schiff bases with glycine and alanine have been synthesized. The greater efficiency of the complexes in terms of faster reaction rates and stereoselectivities in the asymmetric synthesis of (S)-α-amino acids has also been demonstrated.