7622-23-3

Usage

Uses

Used in Pharmaceutical Industry:
Benzenepropanoic acid, a-hydroxy-, 1,1-dimethylethyl ester, (S)is used as an intermediate in the synthetic preparation of various pharmaceutical compounds. Its unique structure and chirality make it a valuable building block for the development of new drugs with potential therapeutic applications.
Used in the Synthesis of Clavatustides:
Specifically, Benzenepropanoic acid, a-hydroxy-, 1,1-dimethylethyl ester, (S)is utilized in the synthetic preparation of clavatustides A (C563723) and B (C563725) and their enantiomers. This is achieved through esterification via ring opening of benzoxazinones, a chemical reaction that allows for the creation of complex molecular structures with potential biological activities.

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 
• 1316671-16-5 (R)-N-(9-fluorenylmethoxycarbonyl)-(S)-pipecolinylphenyllactic acid 
• 1316671-14-3 C₃₄H₃₇NO₆ 

Relevant academic research and scientific papers

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

Total synthesis of the antifungal depsipeptide petriellin A

We report the solid-phase total synthesis of the antifungal highly modified cyclic depsipeptide petriellin A. The synthesis confirms earlier reports on the absolute configuration of the natural product. The solid-phase approach resulted in a protected lin

Zinc-catalyzed enantiospecific sp3-sp3 cross-coupling of α-hydroxy ester triflates with grignard reagents

(Chemical Equation Presented) Zinc chloride does the trick and efficiently catalyzes the enantiospecific cross-coupling of α-hydroxy ester triflates with Grignard reagents under mild conditions. Enantiopure α-hydroxy esters are directly available from the chiral pool or by diazotization of α-amino acids. Substantial variations in both reacting partners are tolerated making this methodology an attractive alternative to enolate alkylation featuring a reversal of polarity.

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.

Asymmetric Synthesis of 2,3-Disubstituted Succinates via Chiral Oxazolidinone Controlled Displacement of α-Trifluoromethanesulfonate Substituted Esters

The addition of chiral imides to α-trifluoromethanesulfonate esters gave chiral 2,3-disubstituted succinates with moderate to excellent diastereoselectivity and in good overall chemical yields.Both syn and anti chiral products are attainable via this methodology, with generally better diastereoselectivity and chemical yields observed in the production of the syn products.The reactions proceed through the predicted SN2 displacement of the triflate leaving group, as inferred from the absolute configuration of the products.