81505-49-9

Usage

Uses

Used in Pharmaceutical Research:
(S)-(-)-Methyl 2-[(tert-butoxycarbonyl)amino]-6-hydroxypentanoate is used as a building block for the synthesis of various biologically active molecules and peptides. Its role in protecting the amino group of valine enhances the efficiency and selectivity of chemical reactions, leading to the development of new pharmaceutical compounds.
Used in Organic Synthesis:
In the field of organic synthesis, (S)-(-)-Methyl 2-[(tert-butoxycarbonyl)amino]-6-hydroxypentanoate is employed as a valuable protecting group for the amino group of valine. This protection allows chemists to carry out selective reactions without affecting the amino group, thus facilitating the synthesis of complex organic molecules with greater precision and control.
Production Methods:
(S)-(-)-Methyl 2-[(tert-butoxycarbonyl)amino]-6-hydroxypentanoate is typically prepared through the condensation of (S)-valine with tert-butyl chloroformate, followed by ester hydrolysis to yield the desired product. This method ensures the selective protection of the amino group, making it a reliable and efficient process for obtaining the compound.

Upstream product

• 55477-80-0 methyl 2-[(tert-butoxycarbonyl)amino]acrylate 
• 627-18-9 1-bromo-3-propanol 
• 172749-96-1 N-[(tert-butoxy)carbonyl]-L-cysteine methyl ester 
• 97347-42-7 (+)-(S)-N₂,N₆-bis[(1,1-dimethylethoxy)carbonyl]-6-oxo-lysine methyl ester 
• 110579-52-7 (E)-(S)-2-tert-Butoxycarbonylamino-6-hydroxy-hex-4-enoic acid methyl ester 
• 2483-48-9 (+)-(S)-N₂,N₆-bis[(1,1-dimethylethoxy)carbonyl]-lysine methyl ester 
• 186581-53-3 diazomethane 
• 77611-37-1 (S)-2-((tert-butoxycarbonyl)amino)-6-hydroxyhexanoic acid 
• 219617-15-9 methyl (S)-2-[di(tert-butoxycarbonyl)amino]-6-oxohexanoate 
• 219617-13-7 dimethyl (S)-2-[di(tert-butoxycarbonyl)amino]hexanedioate 
• 615258-01-0 dimethyl (S)-2-[(tert-butoxycarbonyl)amino]hexanedioate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1118-90-7 L-homoglutamic acid 
• 74-88-4 methyl iodide 

Downstream Products

• 167090-40-6 (S)-2-amino-6-hydroxy-hexanoic acid methyl ester 
• 1079209-08-7 C₁₉H₂₉NO₅ 
• 1460302-83-3 N-[(13S,16R)-16-methyl-14-oxo-18-oxa-8-thia-15-azatricyclo[17.3.1.0²'⁷]tricosa-1⁽²³⁾,2,4,6,19,21-hexaen-13-yl]benzenesulfonamide 
• 1460303-60-9 C₂₉H₃₉N₃O₇S 
• 1460307-04-3 C₃₀H₄₁N₃O₇S 
• 1460307-03-2 C₂₂H₂₆N₂O₅S 
• 1460307-02-1 C₁₈H₂₂N₂O₃S 
• 1460307-01-0 C₂₃H₃₀N₂O₅S 
• 81505-51-3 (D,L)-N²-Boc-N⁶-acetyl-N⁶-(benzyloxy)lysine methyl ester 
• 81505-60-4 6-(Acetyl-benzyloxy-amino)-2-amino-hexanoic acid methyl ester 
• 81505-62-6 N²,N²-(anhydromethylene-1,5-citryl)bis6-acetyl-N⁶-(benzyloxy)-(L)-lysine methyl ester 
• 81505-63-7 N²,N²-(1,5-citryl)bis6-acetyl-N⁶-(benzyloxy)-(L)-lysine> 

Relevant academic research and scientific papers

Synthesis and inhibitory activity of substrate-analog fructosyl peptide oxidase inhibitors

Abstract Fructosyl peptide oxidases (FPOXs) play a crucial role in the diagnosis of diabetes. Their main function is to cleave fructosyl amino acids or fructosyl peptides into glucosone and the corresponding amino acids/dipeptides. In this study, the subs

Combined application of organozinc chemistry and one-pot hydroboration-Suzuki coupling to the synthesis of amino acids

Hydroboration using 9-BBN-H of the protected enantiomerically pure but-3-enylglycine derivative 11, prepared by copper-catalysed allylation of the serine-derived organozinc reagent 1, followed by Suzuki coupling of the derived borane with a variety of aromatic halides, 2-bromopyridine and 2-bromopropene gives the protected amino acids 14a-1 and 15. This method augments our previous methods for the synthesis of phenylalanine homologues.

Cu(OTf)2-Promoted 1,4-addition of alkyl bromides to dehydroalanine

Zn/Cu(OTf)2-mediated addition of alkyl bromides to dehydroalanine (Dha) derivatives including dipeptides and tripeptides in good to high yields under an aqueous medium was developed. This protocol allows selective and biocompatible access to various amino acid units from Dha derivatives.

Catalytic Asymmetric Hydrogenation of Dehydroamino Acid Esters with Biscarbamate Protection and Its Application to the Synthesis of xCT Inhibitors

Catalytic asymmetric hydrogenation of dehydroamino acid esters with biscarbamate protection was examined for the first time to prepare optically active amino acids. The new method was successfully applied to the synthesis of new cystine–glutamate exchanger inhibitors.

CONFORMATIONALLY CONSTRAINED, FULLY SYNTHETIC MACROCYCLIC COMPOUNDS

The conformationally restricted, spatially defined macrocyclic ring system of formula (I) is constituted by three distinct molecular parts: Template A, conformation Modulator B and Bridge C. Macrocycles described by this ring system I are readily manufactured by parallel synthesis or combinatorial chemistry in solution or on solid phase. They are designed to interact with a variety of specific biological target classes, examples being agonistic or antagonistic activity on G-protein coupled receptors (GPCRs), inhibitory activity on enzymes or antimicrobial activity. In particular, these macrocycles show inhibitory activity on endothelin converting enzyme of subtype 1 (ECE-1) and/or the cysteine protease cathepsin S (CatS), and/or act as antagonists of the oxytocin (OT) receptor, thyrotropin-releasing hormone (TRH) receptor and/or leukotriene B4 (LTB4) receptor, and/or as agonists of the bombesin 3 (BB3) receptor, and/or show antimicrobial activity against at least one bacterial strain. Thus they are showing great potential as medicaments for a variety of diseases.

CONFORMATIONALLY CONSTRAINED, FULLY SYNTHETIC MACROCYCLIC COMPOUNDS

The conformationally restricted, spatially defined macrocyclic ring system of formula (I) is constituted by three distinct molecular parts: Template A, conformation Modulator B and Bridge C. Macrocycles described by this ring system I are readily manufactured by parallel synthesis or combinatorial chemistry in solution or on solid phase. They are designed to interact with a variety of specific biological target classes, examples being agonistic or antagonistic activity on G-protein coupled receptors (GPCRs), inhibitory activity on enzymes or antimicrobial activity. In particular, these macrocycles show inhibitory activity on endothelin converting enzyme of subtype 1 (ECE-1 ) and/or the cysteine protease cathepsin S (CatS), and/or act as antagonists of the oxytocin (OT) receptor, thyrotropin-releasing hormone (TRH) receptor and/or leukotriene B4 (LTB4) receptor, and/or as agonists of the bombesin 3 (BB3) receptor, and/or show antimicrobial activity against at least one bacterial strain. Thus they are showing great potential as medicaments for a variety of diseases.

Selective inhibitors of plasmepsin II of Plasmodium falciparum on the basis of pepstatin

A number of new inhibitors of plasmepsin II (PlmII) Plasmodium falciparum, which was one of the key factors of survival of malarial parasite, was synthesized. The inhibitors were analogues of pepstatin with different substitutions for the alanine residue.

A facile synthesis of (S)-gizzerosine, a potent agonist of the histamine H2-receptor

A simple and direct approach for the synthesis of (S)-gizzerosine, an amino acid responsible for the disease, black vomit, and a potent histamine H2-receptor, has been developed in 10 steps and in 31% overall yield from l-aspartic acid. The key steps involved a two-carbon homologation of an l-aspartic acid semi-aldehyde and direct alkylation of unprotected histamine with a 6-hydroxynorleucine derivative.

A novel three-step hydroxy-deamination sequence: Conversion of lysine to 6-hydroxynorleucine derivatives

Oxidation of carbamates with catalytic RuO4, generated from RuO2 and NaBrO3, provides the corresponding acyl carbamates, which can be reduced with NaBH4 to provide alcohols. Application of this methodology to L-lysine provides (S)-6-hydroxynorleucine derivatives.

Microbial Iron Chelators: Total Synthesis of Aerobactin and Its Constiruent Amino Acid, N6-Acetyl-N6-hydroxylysine

The synthesis of the natural ferric ionophore (-)-aerobactin (1) and of its constituent amino acid N6-acetyl-N6-hydroxylysine (2) is described.The benzyl hydroxamates * and ( were subjected to triphenylphosphine-diethyl azodicarboxylate-mediated alkylations with the ε-hydroxynorleucine derivative 7a.While * gave a complex mixture with predominant carbonyl O-alkylation, 9 was cleanly N-alkylated to yield 14.Compounds 10a,b were prepared by direct alkylation of 8 with bromides 15a,b which gave predominant N-alkylation.Hydrogenation of (D,L)-10a yielded (D,L)-N-6- acetyl-N6-hydroxylysine (2).Optically active 10b, prepared from (L)-ε-hydroxynorleucine, was α-N deprotected and coupled with anhydromethylenecitryl chloride (18) to yield 19, which was deprotected in two steps to yield (-)-aerobactin (1).