79479-07-5

Basic information

• Product Name: Methyl N-(tert-butoxycarbonyl)-L-threoninate
• Synonyms: N-(TERT-BUTOXYCARBONYL)-L-THREONINE MET&;N-BOC-L-threonine methylester;(2S,3R)-methyl 2-(tert-butoxycarbonylamino)-3-hydroxybutanoate;(2S, 3S)-2-Tert-butoxycarbonylaMino-3-hydroxy-butyric acid Methyl ester Boc-Thr-OMe;Boc-L-Thr-OMe;Boc-L-threonine methyl ester≥ 98% (HPLC);(Tert-Butoxy)Carbonyl Thr-OMe;N-Boc-L-threonine methyl ester, 97.5%
• CAS NO: 79479-07-5
• Molecular Formula: C₁₀H₁₉NO₅
• Molecular Weight: 233.26156
• Product Categories: Amino Acid Derivatives;Peptide Synthesis;Threonine
• Mol File: 79479-07-5.mol

Chemical Properties

• Boiling Point: 206 °C(lit.)
• Flash Point: 172oC
• Appearance: Yellow/Viscous Liquid
• Density: 1.123g/cm3
• Vapor Pressure: 1.16E-06mmHg at 25°C
• Refractive Index: n20/D 1.45(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform (Sparingly), Dichloromethane (Sparingly), DMF (Sparingly), DMSO (Slig
• PKA: 11.00±0.46(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: Methyl N-(tert-butoxycarbonyl)-L-threoninate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl N-(tert-butoxycarbonyl)-L-threoninate(79479-07-5)
• EPA Substance Registry System: Methyl N-(tert-butoxycarbonyl)-L-threoninate(79479-07-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 79479-07-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methyl N-(tert-butoxycarbonyl)-L-threoninate is used as a pharmaceutical intermediate for the synthesis of various drugs and therapeutic agents. The Boc protecting group allows for selective deprotection and functionalization of the amino group, enabling the incorporation of this compound into complex molecular structures.
Used in Chemical Industry:
Methyl N-(tert-butoxycarbonyl)-L-threoninate is also used as a chemical intermediate in the synthesis of various organic compounds and materials. The methyl ester group can be hydrolyzed or further functionalized, providing a versatile building block for the development of new chemical entities and materials with diverse applications.

InChI:InChI=1/C10H19NO5/c1-6(12)7(8(13)15-5)11-9(14)16-10(2,3)4/h6-7,12H,1-5H3,(H,11,14)/t6-,7+/m1/s1

Upstream product

• 186581-53-3 diazomethane 
• 2592-18-9 Boc-Thr-OH 
• 24424-99-5 di-tert-butyl dicarbonate 
• 39994-75-7 L-threonine methyl ester hydrochloride 
• 41840-28-2 S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 72-19-5 L-threonine 
• 83791-43-9 methyl (4S,5R)-5-methyl-2-carbonyloxazolidine-4-carboxylate 
• 22038-72-8 methyldiazene 
• 77-78-1 dimethyl sulfate 
• 3373-59-9 L-threonine methyl ester 
• 137719-70-1 Boc-L-Thr(Bn)-OMe 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 

Downstream Products

• 1027489-76-4 (2S,3R)-3-[Bis-(4-chloro-benzyloxy)-phosphanyloxy]-2-tert-butoxycarbonylamino-butyric acid methyl ester 
• 56776-41-1 methyl 2-(N-(1,1-dimethylethoxy)methanamido)butenoate 
• 63658-16-2 (Z)-methyl 2-((tertbutoxycarbonyl)amino)but-2-enoate 
• 56776-41-1 (E)-2-N-(tert-butyloxycarbonyl)dehydroaminobutyric acid methyl ester 
• 39994-75-7 L-threonine methyl ester hydrochloride 
• 99216-67-8 2-<<(tert-butoxy)carbonyl>amino>butane-1,3-diol 
• 112380-21-9 N-[(1,1-dimethylethoxy)carbonyl]-O-[(4-methylphenyl)sulfonyl]-L-threonine methyl ester 
• 108149-61-7 3-(tert-butyl) 4-methyl (4S,5R)-2,2,5-trimethyloxazolidine-3,4-dicarboxylate 
• 159846-15-8 N-(tert-Butoxycarbonyl)-O-(tert-butyldiphenylsilyl)-L-threonine methyl ester 
• 80082-48-0 t-butyloxycarbonyl-L-threonine amide 
• 552888-37-6 N-(tert-butoxycarbonyl)-O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-galactopyranosyl)-L-threonine methyl ester 
• 695177-56-1 (2S,3R)-3-[(2S,3R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-3-nitro-4-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-tert-butoxycarbonylamino-butyric acid methyl ester 
• 204187-64-4 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-threo-L-galacto-decitol 
• 213820-05-4 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-decitol 

Relevant articles and documents

Synthesis and Biological Evaluation of CF3Se-Substituted α-Amino Acid Derivatives

Several CF3Se-substituted α-amino acid derivatives, such as (R)-2-amino-3-((trifluoromethyl)selanyl)propanoates (5 a/6 a), (S)-2-amino-4-((trifluoromethyl)selanyl)butanoates (5 b/6 b), (2R,3R)-2-amino-3-((trifluoromethyl)selanyl)butanoates (5 c/6 c), (R)-2-((S)-2-amino-3-phenylpropanamido)-3-((trifluoromethyl)selanyl)propanoates (11 a/12 a), and (R)-2-(2-aminoacetamido)-3-((trifluoromethyl)selanyl)propanoates (11 b/12 b), were readily synthesized from natural amino acids and [Me4N][SeCF3]. The primary in vitro cytotoxicity assays revealed that compounds 6 a, 11 a and 12 a were more effective cell growth inhibitors than the other tested CF3Se-substituted derivatives towards MCF-7, HCT116, and SK-OV-3 cells, with their IC50 values being less than 10 μM for MCF-7 and HCT116 cells. This study indicated the potentials of CF3Se moiety as a pharmaceutically relevant group in the design and synthesis of novel biologically active molecules.

Synthesis and Conformational Analysis of Aminopyrazolonyl Amino Acid (APA)/Peptides

Pyrazole, pyrazolone, and aminopyrazolone derived molecules are bioactive molecules and considered as potential therapeutic drug candidates because of their unique structural properties. These molecules have abilities to interact with several bio-macromolecules via non-covalent interactions such as hydrogen bonding and π–π interactions. In structural organization of dipeptides, pyrazole containing aromatic amino acid/dipeptides have been explored and considered as potential amino acid residue. In repertoire of unnatural aromatic amino acids, this report describes the synthesis of 4-aminopyrazolonyl containing amino acids and their crystal structures. The incorporation of 4-aminopyrazolonyl at N-terminal of native amino acid/dipeptides influences the conformational changes of respective peptide which induces the formation of distinctive supramolecular self-assembly structures such as β-sheet and α-helices in their solid-state crystal. The structural conformation of those peptides, here, are also demonstrated in solution phase by 1H-NMR (1D/2D) and [D6]DMSO titration methods which support the formation of inter-/intramolecular hydrogen bonding in solution. Hence, these unnatural amino acid analogues can tune the secondary structure of natural amino acid/peptides by introducing at N-terminal via amide bond.

Synthesis method of aztreonam monocyclic mother nucleus

The invention discloses a synthesis method of an aztreonam monocyclic mother nucleus, and mainly relates to the technical field of pharmaceutical and chemical industry. The method comprises the stepsthat L-threonine is subjected to methyl esterification; terbutyloxycarbonyl anhydride is used for performing amino BOC protection; ammonia water is subjected to ammonolysis; under the catalysis of a solid basic catalyst, methyl-sulfuric-acyl reaction and sulfonation are performed; cyclization, deprotection and acidification are performed to obtain the aztreonam monocyclic mother nucleus. The raw materials are cheap and can be easily obtained; the yield is high; the cost is low; the synthesis method belongs to a green, energy-saving and environment-friendly practical technology.

Serine- and threonine-derived diamine equivalents for site-specific incorporation of platinum centers in peptides, and the anticancer potential of these conjugates

A modular strategy that allows introduction of one or more reactive platinum units at chosen locations along a peptide sequence is presented. This makes use of diazides generated from serine and threonine as diamine equivalents which can be conjugated to the peptide under standard coupling conditions. Reduction of these diazides using Pd/C and H2 followed by platination affords the final products in good yields. Following this, we prepared a new class of peptide-platinum conjugates and carried out preliminary cytotoxicity evaluation and DNA interaction studies. Inclusion of lysine residues in the sequence was found to improve DNA interaction and anticancer activities compared to analogous conjugates with hydrophobic side chains.

Preparation method of O-methyl-threonine/tyrosine

The invention relates to a preparation method of O-methyl-threonine/tyrosine. The preparation method mainly overcomes the disadvantages of the existing method that a toxic reagent is volatile, the reagent is dangerous, the steps are long, the yield is low, and the like. The preparation method of the O-methyl-threonine/tyrosine comprises the following steps: N-t-butyloxycarboryl-threonine/tyrosineis catalyzed by sodium hydroxide and reacts with dimethyl sulfate to generate N-t-butyloxycarboryl-O-methyl-threonine/tyrosine, and then t-butyloxycarboryl is removed from the N-t-butyloxycarboryl-O-methyl-threonine/tyrosine through acid substances to obtain the product O-methyl-threonine/tyrosine. The product has important application in the fields of antibiotics and polypeptide drugs.

Hydroxy-Directed Amidation of Carboxylic Acid Esters Using a Tantalum Alkoxide Catalyst

We describe herein a new strategy for the chemoselective synthesis of amides by using a metal-catalyzed hydroxy-directed reaction. A hydroxy group located at the β-position of an ester group promoted the activation of a carbonyl group with a tantalum alkoxide catalyst followed by amidation reactions, leading to a wide variety of β-hydroxyamides with excellent chemeselectivity. The chemoselective amidation strategy can be extended to the catalytic synthesis of dipeptide derivatives, which remains challenging research subjects in modern organic synthesis.

Oxidative deselenization of selenocysteine: Applications for programmed ligation at serine

Despite the unique chemical properties of selenocysteine (Sec), ligation at Sec is an under-utilized methodology for protein synthesis. We describe herein an unprecedented protocol for the conversion of Sec to serine (Ser) in a single, high-yielding step.

Phosphine-catalyzed enantioselective γ-addition of 3-substituted oxindoles to 2,3-butadienoates and 2-butynoates: Use of prochiral nucleophiles

The first phosphine-catalyzed enantioselective γ-addition with prochiral nucleophiles and 2,3-butadienoates as the reaction partners has been developed. Both 3-alkyl- and 3-aryl-substituted oxindoles could be employed in this process, which is catalyzed by a chiral phosphine that is derived from an amino acid, thus affording oxindoles that bear an all-carbon quaternary center at the 3-position in high yields and excellent enantioselectivity. The synthetic value of these γ-addition products was demonstrated by the formal total synthesis of two natural products and by the preparation of biologically relevant molecules and structural scaffolds.

A 3,4-trans-fused cyclic protecting group facilitates α-selective catalytic synthesis of 2-deoxyglycosides

A practical approach has been developed to convert glucals and rhamnals into disaccharides or glycoconjugates with high α-selectivity and yields (77-97 %) using a trans-fused cyclic 3,4-O-disiloxane protecting group and TsOH·H2O (1 mol %) as a catalyst. Control of the anomeric selectivity arises from conformational locking of the intermediate oxacarbenium cation. Glucals outperform rhamnals because the C6 side-chain conformation augments the selectivity.

Intramolecular C-H...O hydrogen-bond mediated stabilization of a Cis- D Pro imide-bond in a stereocontrolled heterochiral model peptide

The X-ray diffraction analysis of a stereocontrolled heterochiral designed model peptide Boc-DPro-Thr-OMe (1) revealed the existence of an unusual folded molecular structure, stabilized via an effective unconventional C-H...O type intramolecular hydrogen-bond, encompassing a noncovalent 12-membered ring-motif. Together with an uncommon type a disposition of the urethane moiety, the tightly folded topology is compounded with a cis- DPro imide-bond. The overall conformation is suggested to be the reminiscent of specific type VI β-turn structures, hitherto, characterized across the Aaa-cis-Pro peptide-bonds in globular proteins and polypeptides. The 13C NMR spectrum of 1 in an apolar CDCl3 environment revealed the presence of approximately an equal population of cis and trans isomers unexpectedly, analogous to Pro side-chain, the 13C NMR chemical-shifts of Thr Cβ-resonance is observed to be sensitive toward cis-trans isomerization. In conjunction with solid-state FT-IR spectral data, we established that a network of complex intermolecular hydrogen-bonds stabilize a self-complementary noncovalent helical hexagonal self-assembly and crystallographic supramolecular aggregate. The results incline us to highlight that the stabilization of cis-DPro peptide-bond in crystalline state may be driven by the favorable energy of formation of an unconventional weak C-H...O intramolecular hydrogen-bond. Copyright