57292-45-2

Basic information

• Product Name: BOC-D-4-Fluorophe
• Synonyms: BOC-(R)-2-AMINO-3-(4'-FLUOROPHENYL)PROPANOIC ACID;BOC-P-FLUORO-D-PHENYLALANINE;BOC-P-FLUORO-D-PHE-OH;BOC-4-FLUORO-D-PHE;BOC-4-FLUORO-D-PHENYLALANINE;BOC-4-FLUORO-D-PHE-OH;BOC-D-PHE(P-F)-OH;BOC-D-PHE(4-F)-OH
• CAS NO: 57292-45-2
• Molecular Formula: C₁₄H₁₈FNO₄
• Molecular Weight: 283.3
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;chiral;Phenylalanine [Phe, F];Unusual Amino Acids;Boc-Amino acid series;a-amino
• Mol File: 57292-45-2.mol
• Article Data: 8

Chemical Properties

• Melting Point: 83-86 °C
• Boiling Point: 431.2 °C at 760 mmHg
• Flash Point: 214.6 °C
• Appearance: white to light yellow crystal powder
• Density: 1.1918 (estimate)
• Vapor Pressure: 3.36E-08mmHg at 25°C
• Storage Temp.: Keep Cold
• PKA: 3.87±0.10(Predicted)
• CAS DataBase Reference: BOC-D-4-Fluorophe(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-D-4-Fluorophe(57292-45-2)
• EPA Substance Registry System: BOC-D-4-Fluorophe(57292-45-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-24/25
• WGK Germany: 3
• Hazardous Substances Data: 57292-45-2(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

Boc-D-4-Fluorophenylalanine, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

InChI:InChI=1/C14H18FNO4/c1-14(2,3)20-13(19)16-11(12(17)18)8-9-4-6-10(15)7-5-9/h4-7,11H,8H2,1-3H3,(H,16,19)(H,17,18)/p-1/t11-/m1/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 1534-90-3 D,L-4-fluorophenylalanine Ethyl Ester Hydrochloride 
• 51-65-0 4-Fluorophenylalanine 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 1132-68-9 L-4-fluorophenylalanine 

Downstream Products

• 142995-50-4 (2S,4R)-2-[(S)-1-(Benzyl-methyl-carbamoyl)-2-(4-fluoro-phenyl)-ethylcarbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 135545-01-6 tert-butyl N-[(1S)-1-[(4-fluorophenyl)methyl]-2-[methoxy(methyl)amino]-2-oxo-ethyl]carbamate 
• 189169-90-2 (Boc-Phe(p-F)-NH-)2 
• 1026975-73-4 (E)-(S)-4-[(S)-2-tert-Butoxycarbonylamino-3-(4-fluoro-phenyl)-propionylamino]-5-[(S)-1-(2,4-dimethoxy-benzyl)-2-oxo-piperidin-3-yl]-pent-2-enoic acid ethyl ester 

Relevant articles and documents

Design, Synthesis, and Pharmacokinetic Evaluation of Phosphate and Amino Acid Ester Prodrugs for Improving the Oral Bioavailability of the HIV-1 Protease Inhibitor Atazanavir

Phosphate and amino acid prodrugs of the HIV-1 protease inhibitor (PI) atazanavir (1) were prepared and evaluated to address solubility and absorption limitations. While the phosphate prodrug failed to release 1 in rats, the introduction of a methylene spacer facilitated prodrug activation, but parent exposure was lower than that following direct administration of 1. Val amino acid and Val-Val dipeptides imparted low plasma exposure of the parent, although the exposure of the prodrugs was high, reflecting good absorption. Screening of additional amino acids resulted in the identification of an l-Phe ester that offered an improved exposure of 1 and reduced levels of the circulating prodrug. Further molecular editing focusing on the linker design culminated in the discovery of the self-immolative l-Phe-Sar dipeptide derivative 74 that gave four-fold improved AUC and eight-fold higher Ctrough values of 1 compared with oral administration of the drug itself, demonstrating a successful prodrug approach to the oral delivery of 1.

NOVEL COMPOUNDS WITH DUAL ACTIVITY

The invention generally relate to novel compounds and uses thereof in preventing antifouling by unicellular organisms and in attracting cells from multicellular organisms.

Antiretroviral hydrazine derivatives

The invention relates to compounds of formula STR1 and salts, pharmaceutical compositions, intermediates and processes of preparation thereof.