57224-63-2

Basic information

• Product Name: N-Carbobenzyloxy-L-threonine methyl ester
• Synonyms: N-CARBOBENZOXY-L-THREONINE METHYL ESTER;N-CARBOBENZYLOXY-L-THREONINE METHYL ESTER;N-ALPHA-CARBOBENZOXY-L-THREONINE METHYL ESTER;Z-L-THREONINE METHYL ESTER;Z-THR-OME;Z-THREONINE-OME;L-Threonine, N-(phenylmethoxy)carbonyl-, methyl ester;CBZ-L-THREONINE METHYL ESTER
• CAS NO: 57224-63-2
• Molecular Formula: C₁₃H₁₇NO₅
• Molecular Weight: 267.28
• Mol File: 57224-63-2.mol
• Article Data: 25

Chemical Properties

• Melting Point: 92-94 °C(lit.)
• Boiling Point: 410.46°C (rough estimate)
• Flash Point: 222.7 °C
• Appearance: White/Powder
• Density: 1.2100 (rough estimate)
• Vapor Pressure: 1.09E-08mmHg at 25°C
• Refractive Index: 1.4365
• Storage Temp.: -15°C
• PKA: 10.79±0.46(Predicted)
• Water Solubility: miscible
• BRN: 2220800
• CAS DataBase Reference: N-Carbobenzyloxy-L-threonine methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-Carbobenzyloxy-L-threonine methyl ester(57224-63-2)
• EPA Substance Registry System: N-Carbobenzyloxy-L-threonine methyl ester(57224-63-2)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 57224-63-2(Hazardous Substances Data)

Usage

Chemical Properties

white to off-white powder

InChI:InChI=1/C13H17NO5/c1-9(15)11(12(16)18-2)14-13(17)19-8-10-6-4-3-5-7-10/h3-7,9,11,15H,8H2,1-2H3,(H,14,17)/t9-,11+/m1/s1

Upstream product

• 67-56-1 methanol 
• 5618-95-1 2-benzyloxycarbonylamino-3-hydroxy-butyric acid 
• 186581-53-3 diazomethane 
• 19728-63-3 N-benzyloxycarbonyl-L-treonine 
• 39994-75-7 L-threonine methyl ester hydrochloride 
• 501-53-1 benzyl chloroformate 
• 72-19-5 L-threonine 
• 245115-65-5 (2S)-(benzyloxycarbonylamino)-(3R)-(1,1-dimethylallyloxy)butyric acid methyl ester 
• 39994-75-7 (+/-) threonine methyl ester hydrochloride 
• 39994-75-7 H-DL-aThr-OMe*HCl 
• 113479-92-8 2-Benzyloxycarbonylamino-4-oxo-pentanoic acid methyl ester 
• 74-88-4 methyl iodide 
• 3373-59-9 L-threonine methyl ester 
• 28130-04-3 Z-Thr-OEt 

Downstream Products

• 49705-98-8 benzyl ((2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl)carbamate 
• 52785-41-8 N-benzyloxycarbonyl-O-tert-butylthreonine methyl ester 
• 4144-14-3 methyl (2S,3R)-2-{[(benzyloxy)carbonyl]amino}-3-methoxybutanoate 
• 70561-63-6 Benzyloxycarbonyl-O-methyl-threonin 
• 104410-78-8 (2S,3R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)butanoate 
• 77942-96-2 N-benzyloxycarbonyl-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-L-threonine methyl ester 
• 74024-23-0 N-benzyloxycarbonyl-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-L-threonine methyl ester 
• 161150-55-6 (2R,3R)-2-(benzyloxycarbonyl)amino-1,3-butanediol 
• 60027-55-6 (E)-α-<(Benzyloxycarbonyl)amino>crotonsaeure-methylester 
• 60027-61-4 methyl (2Z)-2-(N-benzyloxycarbonylamino)but-2-enoate 
• 887699-89-0 N-benzyloxycarbonyl-O-(2,3-di-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)]ethylidene-β-D-mannopyranosyl)-L-threonine methyl ester 
• 1015475-00-9 N-benzoyl-O-[methyl 5-amino-5-N,7-O-carbonyl-3,5-dideoxy-8,9-isopropylidene-4-O-(tert-butyldimethylsilyl)-D-glycerol-β-D-galactonon-2-ulopyranosylonate]-L-threonine methyl ester 

Relevant articles and documents

Electrochemical Dimethyl Sulfide-Mediated Esterification of Amino Acids

Dimethyl sulfide-mediated electrochemical synthetic strategy for esterification of amino acids has been reported. A series of amino acids could react smoothly with alcohols, affording the desired esterification products with good efficiency. Importantly, the tolerance of peptides and gram-scale synthesis shed light on the utility of this protocol. Mechanistically, the dimethyl sulfide as a mediator plays an essential role in the transformation of amino acids.

Synthesis method of Fmoc-O-tert-butyl-L-threoninol

The present invention relates to a synthesis method of Fmoc-O-tert-butyl-L-threoninol, and mainly solves the technical problems that in a process of Fmoc-thr(tbu)-oh reduction by sodium borohydride, the reaction temperature is strictly required and a FMoc protecting group is decomposed, resulting in low yield and high cost. The synthesis method of the invention comprises the following steps: a. L-threonine reacts with thionyl chloride to form L-threonine methyl ester hydrochloride; b. the L-threonine methyl ester hydrochloride under the action of sodium hydroxide is reacted with benzyl chloroformate to produce z-thr-ome; c. the Z-thr-ome reacts with introduced isobutene in the presence of methylene chloride and concentrated sulfuric acid, and alkali adjustment treatment is carried out to obtain z-thr (tbu)-ome; d. in the presence of acetone and water, the Z-thr(tbu)-ome is saponified with added alkali to obtain z-thr(tbu)-oh; e. the Z-thr(tbu)-oh is reduced to z-thr(tbu)-ol by sodium borohydride in tetrahydrofuran; f. the z-thr(tbu)-ol is hydrogenated in methanol to obtain H-thr(tbu)-ol; and g. N-(9-fluorenylmethoxycarbonyloxy)succinimide is added to the H-thr(tbu)-ol to obtain the Fmoc-O-tert-butyl -L-threoninol.

Highly efficient and selective phosphorylation of amino acid derivatives and polyols catalysed by 2-aryl-4-(dimethylamino)pyridine-N-oxides-towards kinase-like reactivity

The chemoselective phosphorylation of hydroxyl containing amino acid derivatives and polyols by phosphoryl chlorides catalyzed by 2-aryl-4-(dimethylamino)pyridine-N-oxides is described.