163277-80-3

Basic information

• Product Name: AC-THR(TBU)-OH
• Synonyms: N-ALPHA-ACETYL-O-T-BUTYL-L-THREONINE;AC-THREONINE(TBU)-OH;AC-THR(TBU)-OH;ACETYL-O-T-BUTYL-L-THREONINE;(2S,3R)-2-AcetaMido-3-(tert-butoxy)butanoic acid;N-Acetyl-O-(1,1-dimethylethyl)-L-threonine;Acetyl-O-tert-butyl-L-threonine≥ 99% (HPLC);Ac-L-Thr(tBu)-OH
• CAS NO: 163277-80-3
• Molecular Formula: C₁₀H₁₉NO₄
• Molecular Weight: 217.26
• Mol File: 163277-80-3.mol

Chemical Properties

• Melting Point: 137°C
• Boiling Point: 395.4±37.0 °C(Predicted)
• Appearance: /
• Density: 1.079±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 3.31±0.10(Predicted)
• CAS DataBase Reference: AC-THR(TBU)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: AC-THR(TBU)-OH(163277-80-3)
• EPA Substance Registry System: AC-THR(TBU)-OH(163277-80-3)

Safety Data

• Hazardous Substances Data: 163277-80-3(Hazardous Substances Data)

Usage

General Description

Ac-Thr(t-Bu)-OH is a threonine derivative.

Upstream product

• 4378-13-6 (O-tert-butyl)-L-threonine 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 

Relevant articles and documents

General Fmoc-Based Solid-Phase Synthesis of Complex Depsipeptides Circumventing Problematic Fmoc Removal

Development of an Fmoc-based solid-phase depsipeptide methodology has been hampered by base-promoted fragmentation and diketoperazine formation upon Fmoc group elimination. Such a strategy would be a useful tool given the number of commercially available Fmoc-protected residues. Herein we report that the addition of small percentages of organic acids to the Fmoc-removal cocktail proves effective to circumvent these drawbacks and most importantly, allowed the development of an exclusively solid-phase stepwise methodology to prepare a highly complex depsipeptide with multiple and consecutive esters bonds. Alongside, the optimal protecting group scheme for residue incorporation, which is not as straightforward as it is for traditional peptide synthesis, was explored. The developed stepwise strategy proved effective for the synthesis of a highly complex cyclodepsipeptide, being comparable to the yields obtained when using traditional combined chemistry approaches.

Synthetic studies on threonines. The preparation of protected derivatives of D-allo- and L-allo-threonine for peptide synthesis

N-Acetylated threonine derivatives, having tert-butyl or benzyl-based side-chain protection, form isolable 5(4H)-oxazalones on treatment with N-ethyl-N'-3-dimethylaminopropyl carbodiimide. N-chloroacetylated threonine derivatives, on the other hand, do not form oxazolones so readily. The N-acetylated oxazolones an easily epimerized and lead to diastereoisomeric mixtures of threonine derivatives on hydrolysis with dilute aqueous acid. The components of these mixtures can be separated chromatogaphically, but a useful alternative for the O-benzylated mixture is selective enzymatic hydrolysis using hog kidney acylase. These chemical transformations provide the basis for practical syntheses of protected derivatives of the non-proteinogenic allo-threonines, suitable for use in peptide synthesis.