52785-41-8

Basic information

• Product Name: Z-THR(TBU)-OME
• Synonyms: N-ALPHA-CARBOBENZOXY-L-THREONINE-T-BUTYL ETHER METHYL ESTER;Z-O-T-BUTYL-L-THREONINE METHYL ESTER;Z-THR(TBU)-OME;O-(1,1-Dimethylethyl)-N-[(benzyloxy)carbonyl]-L-threonine methyl ester;methyl N-((benzyloxy)carbonyl)-O-(tert-butyl)-L-threoninate
• CAS NO: 52785-41-8
• Molecular Formula: C₁₇H₂₅NO₅
• Molecular Weight: 323.38
• Mol File: 52785-41-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 444.4±45.0 °C(Predicted)
• Appearance: /
• Density: 1.100±0.06 g/cm3(Predicted)
• PKA: 10.52±0.46(Predicted)
• CAS DataBase Reference: Z-THR(TBU)-OME(CAS DataBase Reference)
• NIST Chemistry Reference: Z-THR(TBU)-OME(52785-41-8)
• EPA Substance Registry System: Z-THR(TBU)-OME(52785-41-8)

Safety Data

• Hazardous Substances Data: 52785-41-8(Hazardous Substances Data)

Usage

General Description

Z-THR(TBU)-OME is a chemical compound with the molecular formula C21H15N3O4. It is a derivative of threonine, an amino acid essential for protein synthesis and nitrogen balance in the body. The compound is commonly used in peptide synthesis and pharmaceutical research due to its stability and bioavailability. The Z-THR(TBU)-OME compound contains a tert-butyl group that enhances its solubility and stability, making it suitable for various applications in the field of organic chemistry. Its structure and properties make it a valuable tool for studying peptide interactions and designing new drug molecules.

Upstream product

• 57224-63-2 methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate 
• 115-11-7 isobutene 
• 83824-81-1 (2S,3S)-3-methylaziridine-1,2-dicarboxylic acid 1-benzylester 2-methyl ester 
• 75-65-0 tert-butyl alcohol 
• 57224-63-2 Z-DL-Thr-OMe 
• 57224-63-2 Z-DL-aThr-OMe 
• 501-53-1 benzyl chloroformate 
• 16966-07-7 (2S,3R)-2-(((benzyloxy)carbonyl)amino)-3-(tert-butoxy)butanoic acid dicyclohexylammonium salt 
• 83860-98-4 (2S,3S)-H-3-MeAzy-OMe 
• 186581-53-3 diazomethane 
• 16966-09-9 N-benzyloxycarbonyl-O-t-butyl-L-threonine 
• 16966-09-9 N-Z-O-tert-butyl-L-threonine 
• 74-88-4 methyl iodide 

Downstream Products

• 16966-09-9 N-benzyloxycarbonyl-O-t-butyl-L-threonine 
• 16966-09-9 Z-DL-Thr(t-Bu)-OH 
• 16966-09-9 Z-DL-aThr(t-Bu)-OH 
• 85308-84-5 ((1S,2R)-2-tert-Butoxy-1-formyl-propyl)-carbamic acid benzyl ester 
• 42417-73-2 Z-N-Me-DL-Thr(t-Bu)-OH 
• 42417-73-2 Z-N-Me-DL-aThr(t-Bu)-OH 
• 189337-28-8 Fmoc-Thr(t-Bu)-ol 
• 1628805-46-8 IDH-305 
• 75189-63-8 N^α'-(triphenylmethylglycyl-asparaginyl-leucyl-O-tert-butylseryl-O-tert-butylthreonyl)-N^α-tert-butyloxycarbonylcystathionine α'-hydrazide 
• 75189-62-7 N^α'-(triphenylmethylglycyl-asparaginyl-leucyl-O-tert-butylseryl-O-tert-butylthreonyl)-N^α-tert-butyloxycarbonylcystathionine α'-methyl ester 
• 75189-60-5 triphenylmethylglycyl-asparaginyl-leucyl-O-tert-butylseryl-O-tert-butylthreonine hydrazide 
• 75189-59-2 triphenylmethylglycyl-asparaginyl-leucyl-O-tert-butylseryl-O-tert-butylthreonine methyl ester 
• 75189-57-0 N-o-nitrobenzenesulphenylasparaginyl-leucyl-O-tert-butylseryl-O-tert-butylthreonine methyl ester 
• 75189-54-7 N-o-nitrobenzenesulphenylleucyl-O-tert-butylseryl-O-tert-butylthreonine methyl ester 

Relevant articles and documents

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.

Anthranilimide-based glycogen phosphorylase inhibitors for the treatment of Type 2 diabetes: 2. Optimization of serine and threonine ether amino acid residues

Optimization of the amino acid residue of a series of anthranilimide-based glycogen phosphorylase inhibitors is described leading to the identification of serine and threonine ether analogs. t-Butylthreonine analog 20 displayed potent in vitro inhibition of GPa, low potential for P450 inhibition, and excellent pharmacokinetic properties.

Design, synthesis, and biological activities of potent and selective somatostatin analogues incorporating novel peptoid residues

We report the synthesis, bioactivity, and structure-activity relationship studies of compounds related to the Merck cyclic hexapeptide c[Pro6-Phe7-D-Trp8-Lys9-Thr10-Phe11], L-363,301 (the n