1463-21-4

Upstream product

• 67-56-1 methanol 
• 72-18-4 L-valine 
• 431-47-0 trifluoroacetic acid-methyl ester 
• 6306-52-1 L-valine methylester hydrochloride 
• 407-25-0 trifluoroacetic anhydride 
• 4070-48-8 L-Valine methyl ester 
• 886207-25-6 2,2,2-trifluoro-N-[2-methyl-1-(2-thioxo-oxazolidine-3-carbonyl)-propyl]-acetamide 
• 24210-19-3 methyl (2S)-3-methyl-[(benzyloxy)carbonylamino]butanoate 
• 66866-64-6 (4S)-4-isopropyl-5-oxo-1,3-oxazolidine-3-carboxylic acid benzyl ester 
• 34241-42-4 sodium (S)-valinate 
• 1447695-69-3 cycloforskamide 

Downstream Products

• 163453-95-0 (S)-3-amino-2,4-dimethylpentan-2-ol 
• 2996-11-4 N-trifluoroacetyl-L-valine-(N'-trityl-hydrazide) 
• 850733-77-6 (3'R,4S)-3-(1'-oxo-3'-mercapto-3'-phenylpropyl)-4-isopropyl-5,5-dimethyl-1,3-oxazolidinone 
• 877377-55-4 N-cinnamoyl-4S-isopropyl-5,5-dimethyloxazolidinethione 
• 597558-53-7 (S)-4-isopropyl-5,5-dimethyl-1,3-oxazolidine-2-thione 

Relevant academic research and scientific papers

Nyuzenamides A and B: Bicyclic Peptides with Antifungal and Cytotoxic Activity from a Marine-Derived Streptomyces sp.

Two bicyclic peptides, nyuzenamides A (1) and B (2), were discovered from Streptomyces isolated from suspended matter in deep sea water collected in the Sea of Japan. Their structures were determined through nuclear magnetic resonance and mass spectrometry analyses in combination with X-ray crystallography and the chiral-phase gas chromatography-mass spectrometry method to comprise ten amino acid residues containing four unusual amino acids along with aromatic acyl units. Both compounds displayed antifungal activity against pathogenic fungi and cytotoxicity against P388 murine leukemia cells.

Cycloforskamide, a cytotoxic macrocyclic peptide from the sea slug Pleurobranchus forskalii

A macrocylic dodecapeptide, cycloforskamide, was isolated from the sea slug Pleurobranchus forskalii, collected off Ishigaki Island, Japan. Its planar structure was deduced by extensive NMR analyses and was further confirmed by MS/MS fragmentation analyses. Finally, the absolute configuration was determined by total hydrolysis and chiral-phase gas chromatographic analysis. This novel dodecapeptide contains three d-amino acids and three thiazoline heterocycles and exhibits cytotoxicity against murine leukemia P388 cells, with an IC 50 of 5.8 μM.

Design, synthesis, and applications of potential substitutes of t-Bu-phosphinooxazoline in Pd-catalyzed asymmetric transformations and their use for the improvement of the enantioselectivity in the Pd-catalyzed allylation reaction of fluorinated allyl enol carbonates

The design, synthesis, and applications of potential substitutes of t-Bu-PHOX in asymmetric catalysis is reported. The design relies on the incorporation of geminal substituents at C5 in combination with a substituent at C4 other than t-butyl (i-Pr, i-Bu, or s-Bu). Most of these new members of the PHOX ligand family behave similarly in terms of stereoinduction to t-Bu-PHOX in three palladium-catalyzed asymmetric transformations. Electronically modified ligands were also prepared and used to improve the enantioselectivity in the Pd-catalyzed allylation reaction of fluorinated allyl enol carbonates.

Kinetic resolution of protected α-amino acid derivatives by a chiral O-nucleophilic acyl transfer catalyst

The kinetic resolution of α-trifluoroacetamido N-acyl oxazolidinethiones using 5-10% of the chiral, nonracemic O-nucleophilic acyl transfer catalyst 2 is described. A variety of substrates participate in this reaction in excellent yields, with s-factors ranging from 20 to 86. Copyright

Mild regeneration of the carboxylic group of amino acid alkyl esters by aqueous methanolic sodium hydrogen carbonate via 5-oxazolidinones

A simple racemization-free procedure allows the regeneration of the carboxylic acid group of amino acid alkyl esters by way of an intermediate 5-oxazolidinone which is hydrolyzed by treatment with sodium hydrogen carbonate in aqueous methanol.

(S)-4-Isopropyl-5,5-dimethyl-1,3-oxazolidinethione as chiral auxiliary for the intramolecular sulfur transfer in α,β-unsaturated N-acylimides, promoted by NbCl5

The 1,3-oxazolidinethione 4 has been synthesized from (S)-valine and used in the intramolecular sulfur transfer in its N-enoyl derivatives in the presence of NbCl5 as catalyst, which, moreover, works as an indicator of the course of the reactio

Enantioselective Cyclopropanation of Allylic Alcohols. The Effect of Zinc Iodide

The effect of zinc iodide on the catalytic, enantioselective cyclopropanation of aliylic alcohols is examined with bis(iodomethyl)zinc as the reagent and bis-methanesulfonamide 7 as the catalyst. Significant rate enhancement was observed when 1 equiv of zinc iodide was present, but more importantly, the enantiomeric excess of the product cyclopropane increased from 80% to 89% for the substrate cinnamyl alcohol. Reaction studies and spectroscopic investigations show that this remarkable influence is the result of reagent modification via a Schlenk equilibrium that produces the more reactive and selective species (iodomethyl)zinc iodide.

Chiral Discrimination in the Liquid Phase: Excess Volumes of Binary Mixtures of Amino Acid Derivatives

Volume changes on mixing the enantiomers of N-trifluoroacetylamino acid methyl esters (N-TFA-amino acid-OMe) were determined at 25 deg C by means of a high-precision vibrating-tube densimeter.The excess molar volume (VE) for the racemic mixtures of N-TFA-Ala-OMe 1, N-TFA-Val-OMe 2, and N-TFA-Leu-OMe 3, were found as VE = 0.0098, -0.0458, and 0.035 cm3 mol-1, respectively.For 2 and 3, these volumetric effects of discriminating interactions between enantiomers in the liquid phase are the largest ever observed.