53940-88-8

Basic information

• Product Name: BOC-ALPHA-METHYL-D-PHE
• Synonyms: BOC-ALPHA-BENZYL-D-ALA;BOC-ALPHA-METHYL-D-PHE;BOC-ALPHA-METHYL-D-PHENYLALANINE;BOC-(R)-2-AMINO-2-METHYL-3-PHENYLPROPANOIC ACID;N-BOC-ALPHA-METHYL-D-PHENYLALANINE;N-BOC-A-METHYL-D-PHENYLALANINE;Boc-D-a-Methylphenylalanine;(S)-N-Boc-2-benzylalanine
• CAS NO: 53940-88-8
• Molecular Formula: C₁₅H₂₁NO₄
• Molecular Weight: 279.33
• Product Categories: Unusual amino acids;unnatural amino acids
• Mol File: 53940-88-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 432.115 °C at 760 mmHg
• Flash Point: 215.135 °C
• Appearance: /
• Density: 1.141 g/cm³
• PKA: 3.92±0.11(Predicted)
• CAS DataBase Reference: BOC-ALPHA-METHYL-D-PHE(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-ALPHA-METHYL-D-PHE(53940-88-8)
• EPA Substance Registry System: BOC-ALPHA-METHYL-D-PHE(53940-88-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 53940-88-8(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 1443008-10-3 (S)-2-amino-N-((1S,2S)-2-hydroxy-1,2-diphenylethyl)-N,2-dimethyl-3-phenylpropanamide 
• 1132-26-9 2-methyl-3-phenylalanine 
• 64384-47-0 2-amino-3-phenyl-2-methylpropanenitrile 
• 103-79-7 1-phenyl-acetone 
• 1393737-29-5 (S)-4-benzyl-3-tert-butoxycarbonyl-4-methyl-2-oxazolidinone 
• 1393737-59-1 (S)-4-benzyl-4-methyl-2-oxazolidinone 
• 1393737-50-2 (S)-(4-benzyl-2-oxazolidinon-4-yl)methyl p-toluenesulfonate 
• 1393737-23-9 diethyl 2-benzyl-2-(N-((S)-α-methylbenzyl)amino)malonate hydrochloride 
• 1393737-47-7 (R)-4-benzyl-4-hydroxymethyl-2-oxazolidinone 
• 1393737-40-0 (4R,αS)-4-benzyl-4-hydroxymethyl-3-(α-methylbenzyl)-2-oxazolidinone 
• 1393737-36-4 (S)-2-benzyl-2-((α-methylbenzyl)amino)-1,3-propanediol 
• 1393737-24-0 diethyl 2-benzyl-2-(N-((S)-α-methylbenzyl)amino)malonate 
• 23239-35-2 (S)-2-amino-2-methyl-3-phenylpropanoic acid 

Downstream Products

• 129713-59-3 N-tert-butoxycarbonyl-L-α-methylphenylalanyl-L-cysteinyl(Acm)-D-tryptophyl-L-leucine methyl ester 
• 74825-82-4 tert-butoxycarbonyl-α-methyl-L-phenylalanyl-L-valine benzyl ester 
• 192064-93-0 (S)-2-((S)-2-tert-Butoxycarbonylamino-2-methyl-3-phenyl-propionylamino)-3-(1H-imidazol-4-yl)-propionic acid methyl ester 
• 1428736-37-1 (2S)-2-[(tert-butoxycarbonyl)amino]-2-methyl-3-phenylpropanamide 
• 1428736-40-6 (2R,5S)-5-benzyl-5-methyl-2-(pyridine-2-yl)imidazolidine-4-one 
• 1428736-42-8 (2S,5S)-5-benzyl-5-methyl-2-(pyridine-2-yl)imidazolidine-4-one 
• 1428736-44-0 (2R,5S)-5-benzyl-2,5-dimethyl-2-(pyridine-2-yl)imidazolidine-4-one 
• 1428736-46-2 (2S,5S)-5-Benzyl-2,5-dimethyl-2-(pyridine-2-yl)imidazolidine-4-one 
• 1159504-84-3 Boc-MePhe-OMe 
• 74814-09-8 Boc-Tyr-D-Ala-Gly-Phe(αMe)-Val-OH 
• 74814-27-0 (S)-2-((S)-2-Amino-2-methyl-3-phenyl-propionylamino)-3-methyl-butyric acid benzyl ester; hydrochloride 
• 74814-07-6 Tyr-D-Ala-Gly-Phe(αMe) 

Relevant articles and documents

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.

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.

Non-enzymatic diastereoselective asymmetric desymmetrization of 2-benzylserinols giving optically active 4-benzyl-4-hydroxymethyl-2- oxazolidinones: Asymmetric syntheses of α-(hydroxymethyl)phenylalanine, N-Boc-α-methylphenylalanine, cericlamine and BIRT-377

A reaction of (S)-2-benzyl-2-(α-methylbenzyl)amino-1,3-propanediol (S)-4a and 2-chloroethyl chloroformate, and the subsequent addition of DBU gave (4R,αS)-4-benzyl-4-hydroxymethyl-3-(α-methylbenzyl)-2-oxazolidinone (4R)-5a (92% de) via a diastereoselective asymmetric desymmetrization process. Debenzylation of (4R)-5a using trifluoromethanesulfonic acid and anisole in MeNO2 gave (R)-4-benzyl-4-hydroxymethyl-2-oxazolidinone (R)-15a, which was converted into (R)-(α-hydroxymethyl)phenylalanine (7) in two steps. N-Boc-α-methylphenylalanine (8), cericlami0ne (9) and BIRT-377 (10) were also synthesized using these asymmetric desymmetrization and debenzylation.