368870-65-9

Usage

Uses

Used in Pharmaceutical Industry:
(2S,4R)-4-((tert-butoxycarbonyl)amino)-2-methyl-5-phenylpentanoic acid is used as a key intermediate in the synthesis of various peptide-based drugs. Its role as a building block allows for the creation of complex peptide structures that can be tailored for specific therapeutic applications, such as antibiotics, antifungals, and antiviral agents.
Used in Organic Chemistry Research:
In the field of organic chemistry, (2S,4R)-4-((tert-butoxycarbonyl)amino)-2-methyl-5-phenylpentanoic acid is utilized as a protecting group for the amine functional group. This protects the amine group from unwanted reactions during the synthesis process, ensuring that the desired peptide or molecule can be obtained with high purity and yield.
Used in Biochemistry Research:
(2S,4R)-4-((tert-butoxycarbonyl)amino)-2-methyl-5-phenylpentanoic acid is also employed in biochemistry research to study the properties and functions of amino acids and peptides. By incorporating (2S,4R)-4-((tert-butoxycarbonyl)amino)-2-methyl-5-phenylpentanoic acid into peptide sequences, researchers can investigate the effects of specific modifications on the structure, stability, and biological activity of peptides.

Upstream product

• 1173283-52-7 C₂₃H₃₄N₂O₅ 
• 156592-93-7 (3S)-4-<(tert-butyldimethylsilyl)oxy>-3-methylbutanol 
• 796039-47-9 (1R,3S)-(1-benzyl-4-hydroxy-3-methylbutyl)carbamic acid tert-butyl ester 
• 204917-42-0 (3S)-4-(tert-butyldimethylsilanyloxy)-3-methylbutyraldehyde 
• 862387-31-3 (S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-butyric acid 
• 71535-50-7 (S)-(+)-2-benzyl-1-(p-tolylsulfonyl)aziridine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 2174-58-5 L-malic acid 
• 1589-82-8 phenylmagnesium bromide 
• 6973-20-2 (S)-methylsuccinic anhydride 
• 1333145-78-0 (3S,5R)-5-benzyl-3-methylpyrrolidin-2-one 
• 3182-95-4 L-Phenylalaninol 
• 63-91-2 L-phenylalanine 

Downstream Products

• 1017624-85-9 (R)-4-tert-butoxycarbonylamino-3-methyl-5-phenylpentanoic acid benzyl ester 
• 919518-59-5 methyl (2S,4R)-4-{[(2-{(1R,3R)-3-[(tert-butoxycarbonyl)amino]-1-hydroxy-4-methylpentyl}-1,3-thiazol-4-yl)carbonyl]amino}-2-methyl-5-phenylpentanoate 
• 1423040-35-0 methyl (2S,4R)-4-{[(2-{(1R,3R)-1-acetoxy-3-[(tert-butoxycarbonyl)amino]-4-methylpentyl}-1,3-thiazol-4-yl)carbonyl]amino}-2-methyl-5-phenylpentanoate 
• 1423040-49-6 methyl (2S,4R)-4-{[(2-{(6S,9R,11R)-6-[(2S)-butan-2-yl]-9-isopropyl-2,2-dimethyl-4,7,13-trioxo-3,12-dioxa-5,8-diazatetradecan-11-yl}-1,3-thiazol-4-yl)carbonyl]amino}-2-methyl-5-phenylpentanoate 
• 1423040-36-1 (R)-benzyl 2-((2S,3S)-1-((1R,3R)-1-acetoxy-1-(4-((2R,4S)-5-methoxy-4-methyl-5-oxo-1-phenylpentan-2-ylcarbamoyl)thiazol-2-yl)-4-methylpentan-3-ylamino)-3-methyl-1-oxopentan-2-ylcarbamoyl)piperidine-1-carboxylate 
• 919518-62-0 methyl (2S,4R)-4-[({2-[(1R,3R)-1-acetoxy-4-methyl-3-{[(2S,3S)-3-methyl-2-({[(2R)-1-methylpiperidin-2-yl]carbonyl}amino)pentanoyl]amino}pentyl]-1,3-thiazol-4-yl}carbonyl)amino]-2-methyl-5-phenylpentanoate 
• 1423117-90-1 C₂₅H₃₅N₃O₅S 
• 943218-34-6 4-({2-[1-acetoxy-3-(2-amino-3-methyl-pentanoylamino)-4-methyl-pentyl]-thiazole-4-carbonyl}-amino)-2-methyl-5-phenyl-pentanoic acid methyl ester 
• 1423040-41-8 C₃₇H₅₅N₅O₇S 
• 919518-38-0 methyl (2S,4R)-4-[(tert-butoxycarbonyl)amino]-2-methyl-5-phenylpentanoate 

Relevant academic research and scientific papers

Tubulysin Synthesis Featuring Stereoselective Catalysis and Highly Convergent Multicomponent Assembly

A concise and modular total synthesis of the highly potent N14-desacetoxytubulysin H (1) has been accomplished in 18 steps in an overall yield of up to 30percent. Our work highlights the complexity-augmenting and route-shortening power of diastereoselective multicomponent reaction (MCR) as well as the role of bulky ligands to perfectly control both the regioselective and diastereoselective synthesis of tubuphenylalanine in just two steps. The total synthesis not only provides an operationally simple and step economy but will also stimulate major advances in the development of new tubulysin analogues.

Synthesis of tubuphenylalanine and epi-tubuphenylalanine via regioselective aziridine ring opening with carbon nucleophiles followed by hydroboration-oxidation of 1,1-substituted amino alkenes

An efficient synthesis of N-Boc-tubuphenylalanine benzyl ester (N-Boc-Tup-OBn, 1a) and N-Boc-epi-tubuphenylalanine benzyl ester (N-Boc-epi-Tup-OBn, 1b) is reported herein. Regioselective aziridine 4 ring opening with carbon nucleophiles followed by hydrob

CYTOTOXIC AND ANTI-MITOTIC COMPOUNDS, AND METHODS OF USING THE SAME

Compounds of general formula (I) having cytotoxic and/or anti-mitotic activity and methods of using such compounds, as well as pharmaceutical compositions comprising such compounds. The compounds may also be conjugated with a targeting moiety, such as an

An enantioselective total synthesis of tubulysin V

Tubulysin V has been enantioselectively synthesized from the units of dipeptide 23, Tuv and Tup. The features of this synthetic strategy is included three portions, the Tuv fragment 17 was diastereoselectively synthesized from the D-malic acid, the stereocenters of the Tup unit was constructed by the asymmetric reduction as well as methylation, and the epimerization for several known methods was successfully avoided by condensation of fragment 19 with 24, and by deprotection with hydrogenation.

Stereoselective total synthesis of tubulysin v

The total synthesis of tubulysin V was accomplished in 1.0% overall yield with linear 13 steps. Our synthetic strategy featured the following two reactions. One is zinc-mediated aza-Barbier reaction of (R)-N-tert- butanesulfinyl imine 8 with β-ester group functionalized allylic bromide 9 to afford the chiral homo-allylic amine (7); the other is to employ the methodology of aqueous indium-mediated aza-Barbier reaction previously developed by our group, giving the chiral homo-allylic amine 13 with high efficiency. The total synthesis of tubulysin V was accomplished in 1.0% overall yield with linear 13 steps. Our synthetic strategy featured the following two reactions. One is zinc-mediated aza-Barbier reaction of (R)-N-tert-butanesulfinyl imine 8 with β-ester group functionalized allylic bromide 9 to afford the chiral homo-allylic amine 7; the other is to employ the methodology of aqueous indium-mediated aza-Barbier reaction previously developed by our group, giving the chiral homo-allylic amine 13 with high efficiency. Copyright

Total syntheses of tubulysins

The total syntheses of tetrapeptides tubulysins D (1b), U (1c), and V (1d), which are potent tubulin polymerization inhibitors, are described. The synthesis of Tuv (2), an unusual amino acid constituent of tubulysins, includes an 1,3-dipolar cycloaddition

Stereoselective synthesis of tubuvaline methyl ester and tubuphenylalanine, components of tubulysins, tubulin polymerization inhibitors

Synthetic studies of two components of tubulysins, tubulin polymerization inhibitors are described. The highly stereoselective synthesis of tubuvaline methyl ester (2) was accomplished by 1,3-dipolar cycloaddition of nitrone d-6 and acrylic acid derivativ

Cytotoxic simplified tubulysin analogues

An efficient route for the synthesis of the tubulysin family of antimitotic peptides was developed. Simplified tubulysin analogues were synthesized to define the minimum pharmacophore required for cytotoxicity. Simplified tubulysin analogues retain signif