60538-19-4

Basic information

• Product Name: methyl (2R,3R)-2-[[(tert-butoxy)carbonyl]amino]-3-hydroxybutanoate
• Synonyms: methyl (2R,3R)-2-[[(tert-butoxy)carbonyl]amino]-3-hydroxybutanoate
• CAS NO: 60538-19-4
• Molecular Weight: 233.265
• Mol File: 60538-19-4.mol
• Article Data: 35

Chemical Properties

• CAS DataBase Reference: methyl (2R,3R)-2-[[(tert-butoxy)carbonyl]amino]-3-hydroxybutanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2R,3R)-2-[[(tert-butoxy)carbonyl]amino]-3-hydroxybutanoate(60538-19-4)
• EPA Substance Registry System: methyl (2R,3R)-2-[[(tert-butoxy)carbonyl]amino]-3-hydroxybutanoate(60538-19-4)

Safety Data

• Hazardous Substances Data: 60538-19-4(Hazardous Substances Data)

Upstream product

• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 39994-75-7 L-threonine methyl ester hydrochloride 
• 67-56-1 methanol 
• 2592-18-9 Boc-Thr-OH 
• 137719-70-1 Boc-L-Thr(Bn)-OMe 
• 24424-99-5 di-tert-butyl dicarbonate 
• 3373-59-9 L-threonine methyl ester 
• 77-78-1 dimethyl sulfate 
• 22038-72-8 methyldiazene 
• 83791-43-9 methyl (4S,5R)-5-methyl-2-carbonyloxazolidine-4-carboxylate 
• 72-19-5 L-threonine 
• 74-88-4 methyl iodide 
• 113525-85-2 methyl N-Boc-(4S,5R)-5-methyl-2-oxazolidinone-4-carboxylate 
• 41840-28-2 S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine 

Downstream Products

• 159846-15-8 N-(tert-Butoxycarbonyl)-O-(tert-butyldiphenylsilyl)-L-threonine methyl ester 
• 80082-48-0 t-butyloxycarbonyl-L-threonine amide 
• 108149-61-7 3-(tert-butyl) 4-methyl (4S,5R)-2,2,5-trimethyloxazolidine-3,4-dicarboxylate 
• 108149-62-8 (4S,5R)-3-(tert-Butoxycarbonyl)-4-formyl-2,2,5-trimethyloxazolidine 
• 300831-66-7 (E)-(1S,4R,6R,13R,14S,18R)-14-tert-Butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-13-methyl-2,15-dioxo-12-oxa-3,16-diaza-tricyclo[14.3.0.0^4,6]nonadec-9-ene-4-carboxylic acid methyl ester 
• 300832-05-7 (E)-(1S,4R,6R,13R,14S,18R)-14-tert-Butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-13-methyl-2,15-dioxo-12-oxa-3,16-diaza-tricyclo[14.3.0.0^4,6]nonadec-9-ene-4-carboxylic acid 
• 300831-65-6 (1R,2R)-1-{[(2S,4R)-1-((2S,3R)-3-Allyloxy-2-tert-butoxycarbonylamino-butyryl)-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-but-3-enyl-cyclopropanecarboxylic acid methyl ester 
• 63658-16-2 (Z)-methyl 2-((tertbutoxycarbonyl)amino)but-2-enoate 
• 1404312-28-2 L-threonine N-[(1,1-dimethylethoxy)carbonyl]-O-(6-O-benzyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl) methyl ester 
• 1404311-99-4 L-threonine N-[(1,1-dimethylethoxy)carbonyl]-O-(6-O-benzyl-2,3-dideoxy-β-D-threo-hex-2-enopyranosyl) methyl ester 
• 1449476-01-0 tert-butyl ((2S,3R)-1-((2-amino-4-bromophenyl)amino)-3-methoxy-1-oxobutan-2-yl)carbamate 
• 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 

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.

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

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.

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.