16966-09-9

Basic information

• Product Name: Z-THR(TBU)-OH
• Synonyms: Z-THR(TBU)-OH;(2S,3R)-2-(((Benzyloxy)carbonyl)amino)-3-(tert-butoxy)butanoic acid;L-Threonine, O-(1,1-dimethylethyl)-N-[(phenylmethoxy)carbonyl]-;Cbz-Thr(tBu)-OH
• CAS NO: 16966-09-9
• Molecular Formula: C₁₆H₂₃NO₅
• Molecular Weight: 309.35752
• Mol File: 16966-09-9.mol

Chemical Properties

• Boiling Point: 470.1°C at 760 mmHg
• Flash Point: 238.1°C
• Appearance: /
• Density: 1.152g/cm³
• Vapor Pressure: 1.22E-09mmHg at 25°C
• Refractive Index: 1.518
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Z-THR(TBU)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-THR(TBU)-OH(16966-09-9)
• EPA Substance Registry System: Z-THR(TBU)-OH(16966-09-9)

Safety Data

• Hazardous Substances Data: 16966-09-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
Z-THR(TBU)-OH is used as a building block for the synthesis of peptide-based drugs and molecules, providing a versatile and protected intermediate in the development process.
Used in Organic Synthesis:
Z-THR(TBU)-OH is used as a protected threonine derivative, allowing for the controlled synthesis of complex organic compounds and facilitating the introduction of threonine residues into target molecules.
Used in Chemical Biology Research:
Z-THR(TBU)-OH is used as a valuable tool for researchers in the field of chemical biology, enabling the exploration of novel bioactive molecules and their interactions with biological systems.

InChI:InChI=1/C16H23NO5/c1-11(22-16(2,3)4)13(14(18)19)17-15(20)21-10-12-8-6-5-7-9-12/h5-9,11,13H,10H2,1-4H3,(H,17,20)(H,18,19)/t11?,13-/m0/s1

Upstream product

• 52785-41-8 N-benzyloxycarbonyl-O-tert-butylthreonine methyl ester 
• 14437-51-5 N-Carbobenzoxy-O-tert.-butyl-L-threonin-tert.-butylester 
• 57224-63-2 methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate 
• 16879-84-8 N-(benzyloxycarbonyl)-L-threonine p-nitrobenzyl ester 
• 19728-63-3 N-benzyloxycarbonyl-L-treonine 
• 501-53-1 benzyl chloroformate 
• 4378-13-6 (O-tert-butyl)-L-threonine 
• 52785-41-8 Z-DL-Thr(t-Bu)-OMe 
• 52785-41-8 Z-DL-aThr(t-Bu)-OMe 
• 16879-87-1 p-Nitrobenzyl N-Benzyloxycarbonyl-(O-t-Butyl) Threoninate 
• 57224-63-2 Z-DL-aThr-OMe 
• 57224-63-2 Z-DL-Thr-OMe 
• 83824-81-1 (2S,3S)-3-methylaziridine-1,2-dicarboxylic acid 1-benzylester 2-methyl ester 
• 16966-07-7 (2S,3R)-2-(((benzyloxy)carbonyl)amino)-3-(tert-butoxy)butanoic acid dicyclohexylammonium salt 

Downstream Products

• 69918-28-1 (2S,3R)-2-Benzyloxycarbonylamino-3-tert-butoxy-butyric acid (1S,2R,3S)-1-methyl-2-(3-methyl-butyryloxy)-3-trityloxymethyl-heptyl ester 
• 27981-26-6 (R)-2-[(1R,2S)-2-((2S,3R)-2-Benzyloxycarbonylamino-3-tert-butoxy-butyryloxy)-1-(3-methyl-butyryloxy)-propyl]-hexanoic acid tert-butyl ester 
• 27981-26-6 (S)-2-[(1S,2R)-2-((2S,3R)-2-Benzyloxycarbonylamino-3-tert-butoxy-butyryloxy)-1-(3-methyl-butyryloxy)-propyl]-hexanoic acid tert-butyl ester 
• 22783-13-7 4-((2S,3R)-2-Benzyloxycarbonylamino-3-tert-butoxy-butyryloxy)-pentanoic acid tert-butyl ester 
• 23413-03-8 Z-Thr(tBu)-Pro-NH₂ 
• 183742-71-4 (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-((2S,3R)-2-benzyloxycarbonylamino-3-tert-butoxy-butyrylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 52785-41-8 N-benzyloxycarbonyl-O-tert-butylthreonine methyl ester 
• 817167-11-6 NH₂-Thr(t-Bu)-NHBn 
• 817167-13-8 NH₂-Glu(O-t-Bu)-Thr(t-Bu)-NHBn 
• 817167-12-7 Cbz-Glu(O-t-Bu)-Thr(t-Bu)-NHBn 
• 104322-31-8 N-benzyloxycarbonyl-L-threonine 2,2,2-trichloroethyl ester 

Relevant articles and documents

COMPOUNDS USEFUL FOR THE TREATMENT OF INFECTION WITH MANNHEIMIA HAEMOLYTICA OR HISTOPHILUS SOMNI

The present invention discloses compounds that are useful in the treatment of respiratory diseases of animals, especially Bovine or Swine Respiratory disease (BRD and SRD)

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.

Efficient and practical procedure for the esterification of the free α-carboxylic acid of amino acid residues with β-(trimethylsilyl)ethoxymethyl chloride and triisopropylsilyl chloride

An efficient and practical procedure for the free α-carboxylic acid esterification of amino acid residues with β-(trimethylsilyl)ethoxymethyl chloride and triisopropylsilyl chloride is described. The reaction takes place under mild conditions and the expected protected amino acids are obtained in good to excellent yields. Our method provides a useful alternative for the C-terminal carboxylic acid protection of amino acids and peptides. Moreover, the removal of such protection was also achieved under mild conditions, without affecting either the other protecting groups at the α-amino moiety and side chains or the optical integrity at the α-position of the amino acid residues. Examples of their use in peptide synthesis are also illustrated.

Selective cleavage of tert-butyl esters in the presence of tert-butyl ethers. Application to the synthesis of tert-butoxy amino acids

We report on the selective cleavage of tert-butyl esters in the presence of tert-butyl ether groups by using trimethylsilyl triflate. The method is especially useful for the synthesis of tert-butyl ethers of N-protected hydroxy amino acids which are valuable building blocks for peptide synthesis.

Studies on 2-Aziridinecarboxylic Acid. VI. Synthesis of β-Alkoxy-α-Amino Acids via Ring-opening Reaction of Aziridine

The reaction of aziridine derivatives having a urethane-type protecting group with several alcohols in the presence of boron trifluoride etherate afford the corresponding optically pure O-alkylserine and O-alkylthreonine derivatives via a ring-opening reaction of aziridine in good yield.

PEPTIDES-XXXVIII. SYNTHESIS OF THE 38-49 FRAGMENT OF A LYSOZYME ANALOGUE

The synthesis of the fully protected (38-49) fragment of a lysozyme analogue was successfully achieved.The two protected subfragments (38-42) and (43-49) were assembled by a stepwise approach in which the α-amino protection was afforded by the benzyloxyca