7622-23-3

Basic information

• Product Name: Benzenepropanoic acid,a-hydroxy-, 1,1-dimethylethyl ester,(S)-
• Synonyms: Benzenepropanoic acid,a-hydroxy-, 1,1-dimethylethyl ester,(S)-;Benzenepropanoic acid,α-hydroxy-, 1,1-dimethylethyl ester, (S)-;(S)-tert-butyl 2-hydroxy-3-phenylpropanoate;TERT-BUTYL (S)-2-HYDROXY-3-PHENYLPROPIONATE
• CAS NO: 7622-23-3
• Molecular Formula: C₁₃H₁₈O₃
• Molecular Weight: 222.28
• Product Categories: API intermediates
• Mol File: 7622-23-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 34 °C
• Boiling Point: 320.3±22.0 °C(Predicted)
• Appearance: /
• Density: 1.077±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 13.00±0.20(Predicted)
• CAS DataBase Reference: Benzenepropanoic acid,a-hydroxy-, 1,1-dimethylethyl ester,(S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenepropanoic acid,a-hydroxy-, 1,1-dimethylethyl ester,(S)-(7622-23-3)
• EPA Substance Registry System: Benzenepropanoic acid,a-hydroxy-, 1,1-dimethylethyl ester,(S)-(7622-23-3)

Safety Data

• Hazardous Substances Data: 7622-23-3(Hazardous Substances Data)

Usage

Uses

(S)-tert-Butyl 2-hydroxy-3-phenylpropanoate is used in the synthetic preparation of clavatustides A (C563723) and B (C563725) and their enantiomers by esterification via ring opening of benzoxazinones

Upstream product

• 7678-28-6 L-tert-butyl 2-acetyloxy-3-phenylpropanoate 
• 20312-36-1 L-3-phenyllactic acid 
• 75-65-0 tert-butyl alcohol 
• 63-91-2 L-phenylalanine 
• 33173-31-8 (S)-3-phenyl-2-acetyloxypropionic acid 

Downstream Products

• 170555-66-5 (-)-(2S)-trifluoromethanesulfonyloxy-3-phenyl-propionic acid tert-butyl ester 
• 174538-88-6 benzyloxycarbonyl D-alanyl L-α-hydroxyhydrocinnamic acid t-butyl ester 
• 380886-37-3 D-tert-butyl 2-phthalimid-N-oxy-3-phenylpropanoate 
• 16367-71-8 t-butyl (RS)-phenylalaninate 
• 380886-42-0 D-tert-butyl 2-p-chlorophenylcarbonyl-aminoxy-3-phenylpropanoate 
• 174538-90-0 benzyloxycarbonyl D-alanyl L-α-hydroxyhydrocinnamic acid 
• 174538-93-3 benzyloxycarbonyl D-alanyl L-α-hydroxyhydrocinnamyl L-valyl D-α-hydroxy hydrocinnamic acid 
• 174538-92-2 benzyloxycarbonyl D-alanyl L-α-hydroxyhydrocinnamyl L-valyl D-α-hydroxy hydrocinnamic acid t-butyl ester 
• 174538-94-4 benzyloxycarbonyl D-alanyl L-α-hydroxyhydrocinnamyl L-valyl D-α-hydroxy hydrocinnamic acid pentafluorophenyl ester 
• 174538-96-6 benzyloxycarbonyl D-alanyl L-α-hydroxyhydrocinnamyl L-valyl D-α-hydroxyhydrocinnamyl D-alanyl L-α-hydroxyhydrocinnamyl L-valyl D-α-hydroxyhydrocinnamic acid t-butyl ester 
• 1309439-98-2 C₂₇H₃₄O₇ 
• 1309439-99-3 C₂₃H₂₆O₇ 
• 1316671-16-5 (R)-N-(9-fluorenylmethoxycarbonyl)-(S)-pipecolinylphenyllactic acid 
• 1316671-14-3 C₃₄H₃₇NO₆ 

Relevant articles and documents

α-Aminoxy Oligopeptides: Synthesis, Secondary Structure, and Cytotoxicity of a New Class of Anticancer Foldamers

α-Aminoxy peptides are peptidomimetic foldamers with high proteolytic and conformational stability. To gain an improved synthetic access to α-aminoxy oligopeptides we used a straightforward combination of solution- and solid-phase-supported methods and obtained oligomers that showed a remarkable anticancer activity against a panel of cancer cell lines. We solved the first X-ray crystal structure of an α-aminoxy peptide with multiple turns around the helical axis. The crystal structure revealed a right-handed 28-helical conformation with precisely two residues per turn and a helical pitch of 5.8 ?. By 2D ROESY experiments, molecular dynamics simulations, and CD spectroscopy we were able to identify the 28-helix as the predominant conformation in organic solvents. In aqueous solution, the α-aminoxy peptides exist in the 28-helical conformation at acidic pH, but exhibit remarkable changes in the secondary structure with increasing pH. The most cytotoxic α-aminoxy peptides have an increased propensity to take up a 28-helical conformation in the presence of a model membrane. This indicates a correlation between the 28-helical conformation and the membranolytic activity observed in mode of action studies, thereby providing novel insights in the folding properties and the biological activity of α-aminoxy peptides.

Benzotriazole-mediated syntheses of depsipeptides and oligoesters

Reactions of O-Pg(α-hydroxyacyl)benzotriazoles with (a) unprotected α-hydroxycarboxylic acids, (b) amino acids, and (c) amines afforded, respectively, chirally pure (a) oligoesters, (b) depsidipeptides, and (c) amide conjugates (yields 52-94%). N-Pg(α-Ami

Synthesis and characterization of chiral N-O turns induced by α-aminoxy acids

Chiral α-aminoxy acids of various side chains were synthesized with high optical purity starting from chiral α-amino acids. The conformations of diamides 13a-e, 15, and 16 were probed by using NMR, FT-IR, and CD spectroscopic methods as well as X-ray crystallography. The right-handed turns with eight-membered-ring intramolecular hydrogen bonds between adjacent residues (called the N-O turns) were found to be preferred for D-aminoxy acid residues, and they were independent of the side chains. The rigid chiral N-O turns should have great potential in molecular design.