16369-14-5

Usage

Uses

Used in Pharmaceutical Industry:
D/L-NORVALINOL is used as a key intermediate in the synthesis of various pharmaceutical compounds, particularly for the preparation of amino-substituted pyrimidine derivatives and other aminoethanethiol derivatives.
Used in Organic Synthesis:
D/L-NORVALINOL is used as a versatile building block in organic synthesis for the development of new chemical entities with potential applications in various fields.
Used in Radiation Protection:
D/L-NORVALINOL is used as a precursor for the synthesis of compounds with potential antiradiation properties, which can be beneficial in the development of radiation protection agents.

InChI:InChI=1/C5H13NO/c1-2-3-5(6)4-7/h5,7H,2-4,6H2,1H3/p+1/t5-/m1/s1

Upstream product

• 2899-90-3 2-nitro-pentan-1-ol 
• 516-06-3 D,L-valine 
• 760-78-1 2-aminopentanoic acid 
• 13893-43-1 ethyl 2-aminopentanoate 
• 10047-10-6 norvaline methyl ester hydrochloride 
• 132949-27-0 1-((S)-2-Methoxy-1-phenyl-ethoxymethyl)-butylamine 
• 6600-40-4 L-Norvaline 
• 29582-96-5 L-norvaline methyl ester 
• 145842-50-8 benzyl N-[(1S)-1-(hydroxymethyl)butyl]carbamate 
• 56558-30-6 methyl L-norvalinate hydrochloride 
• 4146-04-7 DL-2-amino-1-pentanol 
• 64502-89-2 1-hydroxypentan-2-one 
• 2013-12-9 D-norvaline 
• 6600-40-4 L-norvaline 

Downstream Products

• 16112-61-1 4-Propyl-oxazolidon-(2) 
• 69451-78-1 Nicotinic acid 2-[(pyridine-3-carbonyl)-amino]-pentyl ester 
• 137160-75-9 N-(1-Hydroxymethyl-butyl)-butyramide 
• 145842-46-2 (+/-)-2-(acetylamino)pentyl acetate 
• 4293-54-3 2-acetylaminopentan-1-ol 
• 189251-19-2 N-(p-toluenesulfonyl)-2-propylaziridine 
• 260550-89-8 (-)-1-(benzofuran-2-yl)-2-propylaminopentane 
• 19856-81-6 3-propyl-morpholine 
• 19856-55-4 3-propyl-4-[3-(3,4,5-trimethoxy-phenyl)-acryloyl]-morpholine 
• 22724-81-8 L-norvalinol 
• 80696-30-6 (2R)-2-aminopentan-1-ol 
• 179684-02-7 2-(Boc-amino)-1-pentanol 
• 64271-01-8 2,5-di-n-propylpyrazine 
• 246256-62-2 (1-propyl-but-3-enyl)-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Data mining of amine dehydrogenases for the synthesis of enantiopure amino alcohols

Chiral amino alcohols are essential building blocks for the pharmaceutical industry, and are widely present in natural and synthetic bioactive compounds. Amine dehydrogenases (AmDHs) can asymmetrically reduce prochiral ketones with low-cost ammonia to chiral amines and water as by-products, using NAD(P)H as a cofactor under mild conditions, but hydroxy ketones with formation of chiral hydroxy amines have rarely been investigated. In this study, six new bacterial AmDHs derived from amino acid dehydrogenases (AADHs) were identified by data mining, and five out of the six enzymes were able to efficiently reduce 1-hydroxybutan-2-one (1a) to (S)-2-aminobutan-1-ol ((S)-2a) with 19-99% conversions and 99% ee. The five AmDHs were purified and biochemically characterized for reductive amination activity towards substrate 1a with the optimal pH at 8.5 or 9.0 and the optimal temperature at 45 °C, 50 °C or 55 °C, and provided reductive amination of a broad range of prochiral α-hydroxy ketones, and even of a model β-hydroxy ketone leading to β-hydroxy amine with 99% ee. Our study expands the toolbox of AmDHs in the synthesis of chiral amino alcohols.

Enantioselective Synthesis of Chiral Vicinal Amino Alcohols Using Amine Dehydrogenases

Chiral vicinal amino alcohols are an important motif found in many biologically active molecules. In this study, biocatalytic reductive amination of α-hydroxy ketones with ammonia was investigated using engineered amine dehydrogenases (AmDHs) derived from the leucine amino acid dehydrogenase (AADH) from Lysinibacillus fusiformis. The AmDHs thus identified enabled the synthesis of (S)-configured vicinal amino alcohols from the corresponding α-hydroxy ketones in up to 99% conversions and >99% ee. One of the AmDH variants was used to prepare a key intermediate for the antituberculosis pharmaceutical ethambutol.

Palladium-N-heterocyclic carbene (NHC)-catalyzed asymmetric synthesis of indolines through regiodivergent C(sp3)-H activation: Scope and DFT study

Two bulky, chiral, monodentate N-heterocyclic carbene ligands were applied to palladium-catalyzed asymmetric C-H arylation to incorporate C(sp3)-H bond activation. Racemic mixtures of the carbamate starting materials underwent regiodivergent reactions to afford different trans-2,3- substituted indolines. Although this CAr-Calkyl coupling requires high temperatures (140-160°C), chiral induction is high. This regiodivergent reaction, when carried out with enantiopure starting materials, can lead to single structurally different enantiopure products, depending on the catalyst chirality. The C-H activation at a tertiary center was realized only in the case of a cyclopropyl group. No C-H activation takes place alpha to a tertiary center. A detailed DFT study is included and analyses of methyl versus methylene versus methine C-H activation is used to rationalize experimentally observed regio- and enantioselectivities.

Synthesis of imidacloprid derivatives with a chiral alkylated imidazolidine ring and evaluation of their insecticidal activity and affinity to the nicotinic acetylcholine receptor

A series of imidacloprid (IMI) derivatives with an alkylated imidazolidine ring were asymmetrically synthesized to evaluate their insecticidal activity against adult female housefly, Musca domestica, and affinity to the nicotinic acetylcholine receptor of the flies. The bulkier the alkyl group, the lower was the receptor affinity, but the derivatives methylated and ethylated at the R-5-position of the imidazolidine ring were equipotent to the unsubstituted compound. Quantitative structure-activity relationship (QSAR) analysis of the receptor affinity demonstrated that the introduction of a substituent into the imidazolidine ring was fundamentally disadvantageous, but the introduction of a substituent at the R-5-position was permissible in the case of its small size. The binding model of the synthesized derivatives with the receptor supported the QSAR analysis, indicating the existence of space for a short alkyl group around the R-5-position in the ligand-binding site. In addition, positive correlation was observed between the insecticidal activity and receptor affinity, suggesting that the receptor affinity was the primary factor in influencing the insecticidal activity even if the imidazolidine ring was modified.

Diastereoselective synthesis of enantiopure homopropargylic n-tert-butylsulfinylamines

The diastereoselective synthesis of enantiopure homopropargylic amines by propargylation of various N-tert-butylsulfinylimines (tBS-imines) with 1-trimethylsilyl allenylzinc bromide is presented. Georg Thieme Verlag Stuttgart · New York.

COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS

The present invention relates to derivatized cyclofructan compounds, compositions comprising derivatized cyclofructan compounds, and methods of using compositions comprising derivatized cyclofructan compounds for chromatographic separations of chemical species, including enantiomers. Said compositions may comprise a solid support and/or polymers comprising derivatized cyclofructan compounds.

Efficient synthesis of functionalized aziridinium salts

(Chemical Equation Presented) Various aziridinium salts were efficiently prepared from bromination of a series of backbone substituted N,N-bisubstituted β-amino alcohols and isolated via flash column chromatography. The effect of C-substitution, N-substitution, solvent, leaving group, and counter-anions on formation of the isolable aziridinium salts was investigated. 2009 American Chemical Society.

A catalyst-free, convenient construction of eight-membered [1,4]oxazocane-5,8-dione heterocycles from aminoethanols with divinyl succinate

A convenient protocol for the synthesis of [1,4]oxazocane-5,8-dione heterocycles by direct cyclization using 2-substituted aminoethanols and divinyl succinate without any catalysts and additives was established. This strategy is quite simple and effective to obtain eight-membered rings incorporating lactone and lactam functional groups. Georg Thieme Verlag Stuttgart.

Amino alcohol derivatives, method of producing said derivatives and medicaments containing them

Compounds of formula I in which R1denotes hydrogen or methyl R2denotes lower straight-chained or branched alkyl with 1 to 10 carbon atoms R3denotes hydrogen or lower alkyl n denotes 0-12 R4denotes alkyl, alkenyl or alkinyl with 6 to 24 carbon atoms, processes for the production thereof as well as pharmaceutical agents containing these compounds for the treatment of osteoporosis.

Enantioselective synthesis and absolute configuration of (-)-1-(benzofuran-2-yl)-2-propylaminopentane, ((-)-BPAP), a highly potent and selective catecholaminergic activity enhancer

Enantioselective synthesis and absolute configuration of (-)-1-(benzofuran-2-yl)-2-propylaminopentane ((-)-BPAP), which is a highly potent and selective catecholaminergic activity enhancer (CAE) substance, are described. The synthetic approach consists of the coupling reaction of benzofuran with (R)-N-tosyl-2-propylazirizine or (R)-N-methoxy-N-methylnorvaliamide, followed by appropriate modifications of the resulting coupling products. As the results, (-)-BPAP turned out to have the R configuration, which was finally confirmed by X-ray crystallographic analysis.