122818-28-4

Usage

Uses

Used in Pharmaceutical Research:
(S)-2-(Boc-aMino)-3-Methylbutyl 4-Methylbenzenesulfonate is used as a reagent for the synthesis of various organic compounds, particularly pharmaceutical intermediates and building blocks. Its role in the development of new drugs and materials is crucial, as it aids in creating complex molecular structures with specific properties.
Used in Organic Synthesis:
In the field of organic synthesis, (S)-2-(Boc-aMino)-3-Methylbutyl 4-Methylbenzenesulfonate is utilized as a versatile and selective reagent for the protection of amine groups in organic reactions. This protection is essential for preventing unwanted side reactions and ensuring the desired product formation.
Used in Amino Acid Derivatives and Peptide Synthesis:
(S)-2-(Boc-aMino)-3-Methylbutyl 4-Methylbenzenesulfonate is also employed in the preparation of amino acid derivatives and peptide synthesis. Its presence ensures the correct formation of peptide bonds and the overall structure of the peptide, which is vital for its biological activity and function.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
Furthermore, (S)-2-(Boc-aMino)-3-Methylbutyl 4-Methylbenzenesulfonate can be used as a chiral auxiliary in asymmetric synthesis. This application allows for the control of the stereochemistry of chemical reactions, leading to the production of enantiomerically pure compounds with specific biological activities.
Overall, (S)-2-(Boc-aMino)-3-Methylbutyl 4-Methylbenzenesulfonate is a valuable compound in the pharmaceutical and chemical industries, contributing to the development of new drugs, materials, and synthetic methods.

Upstream product

• 4124-41-8 p-toluenesulfonylanhydride 
• 2026-48-4 (S)-valinol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 4070-48-8 L-Valine methyl ester 
• 79069-14-0 (S)-2-<(tert-butoxycarbonyl)amino>-3-methylbutan-1-ol 
• 58561-04-9 N-tert-butoxycarbonyl-L-valine methyl ester 
• 110694-59-2 N-tertbutyloxycarbonyl-S-valine methyl ester 
• 72-18-4 L-valine 
• 13734-41-3 t-Boc-L-valine 
• 98-59-9 p-toluenesulfonyl chloride 
• 6306-52-1 L-valine methylester hydrochloride 

Downstream Products

• 172695-23-7 (R)-3-<(tert-butoxycarbonyl)amino>-4-methylpentanenitrile 
• 109687-68-5 (S)-N-tert-butoxycarbonyl-2-amino-3-methyl-1-thiophenylbutane 
• 156358-28-0 (S)-3-methyl-1-(phenylthio)-2-butanamine 
• 206351-72-6 (S)-N'-[1-[(diphenylphosphino)methyl]-2-methylpropyl]-N,N-dimethylmethanimidamide 
• 129972-69-6 <(2S)-3-methyl-2-(trifluoromethylsulfonylamino)butyl>diphenylphosphino 
• 1185453-86-4 C₁₆H₂₄BrNO₂S 
• 1185453-99-9 C₁₁H₁₆BrNS 
• 1643565-07-4 (S)-tert-butyl 6-isopropyl-3-(4-methoxyphenyl)-6,7-dihydro[1,2,3]triazolo[1,5-a]pyrazine-5(4H)carboxylate 
• 146476-35-9 (1S)-[1-[(diphenylphosphino)methyl]-2-methylpropyl]carbamic acid 1,1-dimethylethyl ester 

Relevant academic research and scientific papers

A new class of C2-symmetric diphosphine ligands derived from valine: Remarkably diverse behavior in catalytic asymmetric transformations

A new C2-symmetric diphosphine ligand 8a was readily prepared in one step by treatment of the synthetic precursor of VALAP, 7, with phthaloyl chloride. Remarkably high levels of asymmetric induction, over 99% ee, were achieved using 8a in palladium-catalyzed asymmetric allylic transformations of sterically less demanding cyclohexenyl substrates 9. The ligand system was easily extended to the development of analogous chiral auxiliaries 8b,c by the identical procedure but using isophthaloyl chloride and succinyl chloride. However, the ligands 8b,c exhibited much lower catalytic activity. In contrast to the asymmetric allylic substitutions, 8c demonstrated significant improvement of enantioselectivity, up to 64% ee, in rhodium- catalyzed asymmetric hydrosilylations of acetophenone 11a compared to 35% ee using 8a. In this way, the versatility of the present ligand system played an important role in variations of substrates and reaction types. (C) 1999 Elsevier Science Ltd.

Design, synthesis, and structure-activity relationship studies of L-amino alcohol derivatives as broad-spectrum antifungal agents

To discover broad spectrum antifungal agents, two strategies were applied, and a novel class of L-amino alcohol derivatives were designed and synthesized. 3-F substituted compounds 14i, 14n, 14s and 14v exhibited excellent antifungal activities with broad antifungal spectra against C. albicans and C. tropicalis, with MIC values in the range of 0.03–0.06 μg/mL, and against A. fumigatus and C. neoformans, with MIC values in the range of 1–2 μg/mL. Notably, Compounds 14i, 14n, 14s and 14v also displayed moderate activities against fluconazole-resistance strains 17# and CaR that were isolated from AIDS patients. Moreover, only compounds in the S-configuration showed antifungal activity. Preliminary mechanistic studies showed that the potent antifungal activity of compound 14v stemmed from inhibition of C. albicans CYP51. Compounds 14n and 14v were almost nontoxic to mammalian A549 cells, and their stability in human plasma was excellent.

A rapid entry to amino acid derived diverse 3,4-dihydropyrazines and dihydro[1,2,3]triazolo[1,5-a]pyrazines through 1,3-dipolar cycloaddition

An efficient, general and practical synthesis of diverse 3,4-dihydropyrazines, 6,7-dihydro-[1,2,3]triazolopyrazines and 7,8-dihydro-[1,2,3]triazolodiazepines through intramolecular 1,3-dipolar cycloaddition from amino acid derived common intermediates with high yields is described. Moreover, one-pot access to optically active 3-aryl substituted 6,7-dihydro-[1,2,3]triazolo[1,5-a]pyrazines in the palladium-copper co-catalytic system has also been achieved in this work. The easy substrate availability and operational simplicity make the process suitable for further exploration. This journal is the Partner Organisations 2014.

Synthesis of iron P-N-P' and P-NH-P asymmetric hydrogenation catalysts

Complexes of the type mer,trans-[Fe(P-N-P)(CO)2Br]BF4 are known to be precatalysts for the asymmetric direct hydrogenation of ketones and imines. Employing related ligand scaffolds, we successfully generated and tested the series of three new precatalysts [Fe(PCy2CH2CH-NCH(R)CH2PPh2)(CO)2Br]BF4 with chirality derived from (S)-amino alcohols with phenyl, benzyl, and isopropyl substituents (R), yielding fairly active and selective systems. For the reduction of acetophenone to (S)-1-phenylethanol turnover frequencies up to 920 h-1 and up to 74% enantiomeric excess at 50 °C and 5-25 atm of H2 were obtained. We found, however, that placing these large groups R next to nitrogen was found to be deleterious to catalytic activity. Extending the scope of the ligand structure, we then developed a series of six P-N-P and five P-NH-P systems starting with o-diphenylphosphinobenzaldehyde and the phosphine-amines PPh2CHR1CHR2NH2 (R1 = H, Ph, CH2Ph, iPr with R2 = H or R1 = Me, Ph with R2 = Ph) as well as their corresponding [Fe(P-N-P)(NCMe)3][BF4]2 and [Fe(P-NH-P)(NCMe)3][BF4]2 complexes, which were not catalytically active. Finally, we made the new achiral iron complex mer,cis-Fe(PPh2(o-C6H4)CHNCH2CH2PPh2)(CO)Br2, which was active for the direct hydrogenation of acetophenone, achieving turnover frequencies of 800 h-1 at 50°C and 25 atm of H2.

Syntheis of new chiral 5,6,7,8-tetrahydrotetrazolo[1,5-a]pyrazines from α-amino acid derivatives following "click" chemistry

An efficient and practical synthesis of new chiral fused tetrazoles have been synthesized following [3+2] cycloaddition reaction starting from α-amino acid derivatives.

Synthesis of new chiral 4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyrazines from α-amino acid derivatives under mild conditions

A practical and efficient regioselective synthesis of several new chiral 4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyrazines is described from α-amino acid derivatives following intramolecular 'click' reaction as the key step. The method obviates product pu

Radical addition approach to asymmetric amine synthesis: Design, implementation, and comparison of chiral N-acylhydrazones

Intermolecular radical addition to C=N bonds with acyclic stereocontrol offers excellent potential as a mild, nonbasic carbon-carbon bond construction approach to chiral amines. Here, complete details of the first radical additions to chiral N-acylhydrazones as an approach to asymmetric amine synthesis are disclosed. Novel N-acylhydrazones were designed as chiral C=N radical acceptors with Lewis acid activation, restriction of conformational mobility, and commercial availability of precursors. Amination of 4-alkyl-2-oxazolidinones with O-(mesitylenesulfonyl)hydroxylamine or O-(p-nitrobenzoyl)hydroxylamine afforded N-aminooxazolidinones which were condensed with aldehydes to afford N-acylhydrazones 3-8. Three synthetic methods were developed, implementing these N-acylhydrazones in Lewis acid-promoted intermolecular radical additions to C=N bonds. First, additions of various secondary and tertiary alkyl iodides to propionaldehyde and benzaldehyde hydrazones (3 and 7) under tin hydride radical chain conditions in the presence of ZnCl2 gave N-acylhydrazine adducts with diastereomeric ratios ranging from 93:7 to 99:1. Radical additions to a series of N-acylhydrazones with different substituents on the oxazolidinone revealed that benzyl and diphenylmethyl were more effective stereocontrol elements than those with the aromatic ring directly attached to the oxazolidinone. Second, a tin-free method, exploiting dual functions of triethylborane for both initiation and chain propagation, enabled improved yields in addition of secondary alkyl iodides. Third, under photolytic conditions with hexamethylditin, primary radical addition could be achieved with ethyl iodide in the presence of diethyl ether as cosolvent; the 1-ethoxyethyl adduct was observed as a minor product. Chloromethyl addition was achieved under both the tin-free and photolytic conditions; in this case, the adduct bears alkyl chloride functionality with potential for further elaboration.

Synthesis and reactivities of enantiomerically pure β hydroxyalkyl and β-aminoalkyl ferrocenyl sulfides

Enantiomerically pure β-hydroxyalkyl and β-aminoalkyl ferrocenyl sulfides have been synthesized in good yields from mercaptoferrocene and amino alcohol derivatives. Primary β-aminoalkyl sulfides allowed the synthesis of tetrahydro-1,4-thiazepines containing the ferrocene moiety with good diastereoselectivity and β-iminoalkyl sulfides. Some of these derivatives have successfully been employed as ligands for palladium-catalyzed allylic substitution, with asymmetric induction of up to 99% ee. ( Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

Stereoselective synthesis of 2-alkenylaziridines and 2-alkenylazetidines by palladium-catalyzed intramolecular amination of α- and β-amino allenes

Whereas palladium-catalyzed reaction of N-arylsulfonyl-α-amino allenes with an aryl iodide (4 equiv) in the presence of potassium carbonate (4 equiv) in DMF at around 70 °C affords the corresponding 3-pyrroline derivatives, the reaction in refluxing 1,4-dioxane under otherwise identical conditions yields exclusively or most predominantly the corresponding 2-alkenylaziridines bearing an aryl group on the double bond. Similarly, N-arylsulfonyl-β-amino allenes can be also cyclized into the corresponding alkenylazetidines bearing a 2,4-cis-configuration under palladium-catalyzed cyclization conditions in DMF.

Synthesis of heterofunctionalized multidentate diphosphines

The synthesis of new chiral multidentate amino- and amidophosphine ligands bearing up to six potential coordination sites were synthesized starting from L-valine. Based on these compounds chiral Ru(II) complexes were prepared, characterized and tested in the asymmetric transfer hydrogenation of aryl-alkyl ketones. In all cases investigated the catalyst bearing additional hydroxy groups gave lower conversions than the complex without hydroxy groups. Highest enantioselectivity was achieved with isobutyrophenone as substrate (69%ee). (C) 2000 Elsevier Science Ltd.