143060-31-5

Basic information

• Product Name: (R)-N-Boc-2-amino-3,3-diphenylpropionic acid
• Synonyms: BOC-D-3,3-DIPHENYLALANINE;BOC-D-(3-PHENYL)PHE-OH;BOC-D-ALA(3,3-DIPHENYL)-OH;BOC-D-DPH-OH;n-(tert-butoxycarbonyl)-β-phenyl-d-phenylalanine;3,3-Diphenyl-D-alanine, N-BOC protected;N-Boc-β-phenyl-D-phenylalanine;(R)-N-Boc-2-amino-3,3-diphenylpropionic acid
• CAS NO: 143060-31-5
• Molecular Formula: C₂₀H₂₃NO₄
• Molecular Weight: 341.4
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Amino Acid Derivatives;Chiral Compound;Peptide Synthesis;Phenylalanine Derivatives;Unnatural Amino Acid Derivatives;a-amino;unnatural amino acids
• Mol File: 143060-31-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 157 °C (dec.)(lit.)
• Boiling Point: 502.7 °C at 760 mmHg
• Flash Point: 257.8 °C
• Appearance: /
• Density: 1.167 g/cm³
• Refractive Index: 1.56
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.68±0.10(Predicted)
• CAS DataBase Reference: (R)-N-Boc-2-amino-3,3-diphenylpropionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-N-Boc-2-amino-3,3-diphenylpropionic acid(143060-31-5)
• EPA Substance Registry System: (R)-N-Boc-2-amino-3,3-diphenylpropionic acid(143060-31-5)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• Hazardous Substances Data: 143060-31-5(Hazardous Substances Data)

Usage

General Description

The chemical (R)-N-Boc-2-amino-3,3-diphenylpropionic acid is a compound with a molecular formula of C21H23NO4. It is a chiral, non-proteinogenic amino acid derivative, commonly used as a building block in organic synthesis. (R)-N-Boc-2-amino-3,3-diphenylpropionic acid is usually formed by the condensation of Boc-protected 2-amino-3-phenylpropanoic acid with an aromatic aldehyde in the presence of a suitable catalyst. (R)-N-Boc-2-amino-3,3-diphenylpropionic acid is widely utilized in the pharmaceutical and agrochemical industry for the synthesis of various complex molecules and lead compounds due to its unique structural and stereochemical properties. It is also used in the production of peptides and peptidomimetics for drug discovery and development.

InChI:InChI=1/C20H23NO4/c1-20(2,3)25-19(24)21-17(18(22)23)13-14-8-7-11-16(12-14)15-9-5-4-6-10-15/h4-12,17H,13H2,1-3H3,(H,21,24)(H,22,23)/t17-/m1/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 149597-91-1 (2R)-3,3-diphenylalanine 
• 142956-09-0 (4R,5S)-3-((R)-2-Azido-3,3-diphenyl-propionyl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 142956-07-8 (4R,5S)-3-(3,3-Diphenyl-propionyl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 142956-11-4 (2R)-Azido-3,3-diphenylpropionic acid 
• 142956-06-7 C₂₀H₂₂O₃ 
• 37089-77-3 3,3-diphenylpropanoyl chloride 
• 606-83-7 3,3-Diphenylpropionic acid 
• 173604-34-7 (R)-4-Benzhydryl-2-oxo-oxazolidine-3-carboxylic acid tert-butyl ester 
• 173604-32-5 (S)-4-(hydroxydiphenylmethyl)oxazolidin-2-one 
• 173604-33-6 (4R)-4-(diphenylmethyl)-2-oxazolidinone 
• 459174-50-6 2(S)-{N-[(R)-α-methylbenzyl]amino}-3-O-acetyl-1,1-diphenyl-1,3-propanediol 
• 459174-51-7 2(S)-{N-[(R)-α-methylbenzyl]amino}-1,1-diphenyl-1,3-propanediol 
• 444814-26-0 N-[(R)-α-methylbenzyl]aziridine-2(S)-diphenylmethanol 

Downstream Products

• 143060-93-9 (R)-β,β-diphenyl-α-alanine hydrochloride 
• 872323-61-0 (3R,4S)-3-amino-1-methoxy-4-phenyl-3,4-dihydroquinolin-2(1H)-one hydrochloride 
• 1194096-67-7 ((S)-1-[(R)-1-[(6-amino-pyridin-3-ylmethyl)-carbamoyl]-2,2-dicyclohexyl-ethylcarbamoyl]-2-methylbutyl)carbamic acid tert-butyl ester 
• 1300006-88-5 N-{(R)-1-[(6-amino-pyridin-3-ylmethyl)-carbamoyl]-2,2-dicyclohexyl-ethyl}-2-hydroxy-2-methyl-propionamide trifluoroacetate 
• 1194096-64-4 {(R)-1-[(6-amino-pyridin-3-ylmethyl)-carbamoyl]-2,2-dicyclohexyl-ethyl}-carbamic acid tert-butyl ester 

Relevant articles and documents

Remote Construction of Chiral Vicinal Tertiary and Quaternary Centers by Catalytic Asymmetric 1,6-Conjugate Addition of Prochiral Carbon Nucleophiles to Cyclic Dienones

An unprecedented remote construction of chiral vicinal tertiary and quaternary centers by a catalytic asymmetric 1,6-conjugate addition of prochiral carbon nucleophiles to cyclic dienones has been developed. Both 5H-oxazol-4-ones and 2-oxindoles were found to be very efficient carbon nucleophiles in this reaction at a remote position, giving products with excellent enantio- and diastereoselectivities (up to 99 % ee and >19:1 d.r. for 5H-oxazol-4-ones and up to 97 % ee and >19:1 d.r. for 2-oxindoles).

An efficient synthesis of N-Boc-D-diphenylalanine from a chiral azirdine-2-carboxylate

N-Boc-D-diphenylalanine was prepared from a commercially available aziridine-2(S)-carboxylate through alkylation, regiospecific aziridine ring opening, and benzylic deoxygenation followed by oxidation in 57% overall yield.

Stereocontrolled Conversion of L-Serine into a Series of Valuable Unnatural α-Amino Acids

Stereocontrolled synthesis of (2R,3S)- and (2R,3R)-phenylserine, (R)-3,3-diphenylserine and (R)-3,3-diphenylalanine are described.