155836-48-9

Basic information

• Product Name: N-Boc-beta-phenyl-D-phenylalaninol
• Synonyms: CARBAMIC ACID, [1-(HYDROXYMETHYL)-2,2-DIPHENYLETHYL]-,1,1-DIMETHYLETHYL ESTER, (R)-;(R)-N-(TERT-BUTOXYCARBONYL)-BETA-PHENYL-PHENYLALANINOL;N-(TERT-BUTOXYCARBONYL)-3-PHENYL-D-PHENYLALANINOL;N-(TERT-BUTOXYCARBONYL)-BETA-PHENYL-D-PHENYLALANINOL;N-BOC-BETA-PHENYL-D-PHENYLALANINOL;N-(TERT-BUTOXYCARBONYL)-BETA-PHENYL-D-PH;n-(tert-butoxycarbonyl)-β-phenyl-d-phenylalaninol;(R)-2-Amino-3,3-diphenylpropan-1-ol, N-BOC protected
• CAS NO: 155836-48-9
• Molecular Formula: C₂₀H₂₅NO₃
• Molecular Weight: 327.42
• EINECS: 604-604-1
• Product Categories: Chiral Compound
• Mol File: 155836-48-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 114-116 °C(lit.)
• Boiling Point: 501.207 °C at 760 mmHg
• Flash Point: 256.921 °C
• Appearance: /
• Density: 1.109 g/cm³
• Refractive Index: 1.553
• Storage Temp.: 2-8°C
• CAS DataBase Reference: N-Boc-beta-phenyl-D-phenylalaninol(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-beta-phenyl-D-phenylalaninol(155836-48-9)
• EPA Substance Registry System: N-Boc-beta-phenyl-D-phenylalaninol(155836-48-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 155836-48-9(Hazardous Substances Data)

Usage

General Description

N-Boc-beta-phenyl-D-phenylalaninol is a chemical compound that is commonly used in organic synthesis and drug development. It is a derivative of D-phenylalanine, a naturally occurring amino acid. The "N-Boc" group refers to the tert-butyloxycarbonyl protecting group, which is often used to protect amines during chemical reactions. The beta-phenyl group and the alcohol functionality make this compound a versatile building block in the synthesis of pharmaceuticals and other biologically active molecules. Its chiral nature, due to the presence of the D-phenylalanine moiety, also makes it valuable in the production of enantiomerically pure compounds. Overall, N-Boc-beta-phenyl-D-phenylalaninol is a valuable tool in chemical research and drug discovery.

InChI:InChI=1/C20H25NO3/c1-20(2,3)24-19(23)21-18(14-22)13-15-8-7-11-17(12-15)16-9-5-4-6-10-16/h4-12,18,22H,13-14H2,1-3H3,(H,21,23)/t18-/m1/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 171037-01-7 (R)-2-amino-3,3-diphenyl-1-propanol 
• 173604-34-7 (R)-4-Benzhydryl-2-oxo-oxazolidine-3-carboxylic acid tert-butyl ester 
• 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 
• 459174-50-6 2(S)-{N-[(R)-α-methylbenzyl]amino}-3-O-acetyl-1,1-diphenyl-1,3-propanediol 
• 173604-33-6 (4R)-4-(diphenylmethyl)-2-oxazolidinone 
• 173604-32-5 (S)-4-(hydroxydiphenylmethyl)oxazolidin-2-one 
• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 95715-86-9 (S)-2,2-dimethyl-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester 
• 170937-75-4 (S)-N-tert-butoxycarbonyl-4-(hydroxydiphenylmethyl)-2,2-dimethyloxazolidine 

Downstream Products

• 143060-31-5 N-(tert-butoxycarbonyl)-3,3-diphenyl-D-alanine 
• 171037-01-7 (R)-2-amino-3,3-diphenyl-1-propanol 
• 1246617-14-0 C₂₈H₂₈N₂O₄ 
• 1246617-15-1 C₂₀H₂₆N₂O₂ 
• 1246617-16-2 C₃₆H₃₈N₂O₈ 
• 1246617-17-3 C₃₀H₂₆N₂O₅ 
• 1246617-18-4 C₃₁H₂₈N₂O₅ 
• 1246617-19-5 C₃₀H₂₆N₂O₅ 
• 1246617-20-8 C₂₃H₂₀N₂O₅ 

Relevant articles and documents

Catalytic Enantioselective Direct Aldol Addition of Aryl Ketones to α-Fluorinated Ketones

The catalytic enantioselective synthesis of α-fluorinated chiral tertiary alcohols from (hetero)aryl methyl ketones is described. The use of a bifunctional iminophosphorane (BIMP) superbase was found to facilitate direct aldol addition by providing the strong Br?nsted basicity required for rapid aryl enolate formation. The new synthetic protocol is easy to perform and tolerates a broad range of functionalities and heterocycles with high enantioselectivity (up to >99:1 e.r.). Multi-gram scalability has been demonstrated along with catalyst recovery and recycling. 1H NMR studies identified a 1400-fold rate enhancement under BIMP catalysis, compared to the prior state-of-the-art catalytic system. The utility of the aldol products has been highlighted with the synthesis of various enantioenriched building blocks and heterocycles, including 1,3-aminoalcohol, 1,3-diol, oxetane, and isoxazoline derivatives.

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.