119221-16-8

Basic information

• Product Name: (2R,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutanoic acid
• Synonyms: (2R,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutanoic acid
• CAS NO: 119221-16-8
• Molecular Weight: 253.255
• Mol File: 119221-16-8.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: (2R,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutanoic acid(119221-16-8)
• EPA Substance Registry System: (2R,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutanoic acid(119221-16-8)

Safety Data

• Hazardous Substances Data: 119221-16-8(Hazardous Substances Data)

Usage

Description

(2R,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutanoic acid, also known as Boc-Glu(OtBu)-OH, is a chiral compound derived from glutamic acid, a nonessential amino acid and neurotransmitter in the human body. It is utilized as a building block in peptide synthesis and serves as a protecting group for the carboxyl group of glutamic acid. The chemical structure of Boc-Glu(OtBu)-OH features a benzyl group, a carbonyl group, and a hydroxybutanoic acid moiety, making it a versatile component in peptide chemistry.

Uses

Used in Pharmaceutical Industry:
(2R,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutanoic acid is used as a building block in the synthesis of peptides and proteins for various pharmaceutical applications. Its role as a protecting group for the carboxyl group of glutamic acid allows for the controlled formation of peptide bonds, which is crucial in the development of new drugs and therapeutic agents.
Used in Chemical Synthesis:
In the field of chemical synthesis, (2R,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutanoic acid is used as a protecting group for the carboxyl group of glutamic acid. This enables chemists to carry out selective reactions and synthesize complex peptide structures with greater precision and control.
Used in Research and Development:
(2R,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutanoic acid is employed in research and development for the study of peptide synthesis, protein structure, and function. Its use as a protecting group allows researchers to investigate the properties and interactions of peptides and proteins in a controlled manner, contributing to the advancement of scientific knowledge in these areas.

Upstream product

• 72-19-5 D-threonine 
• 501-53-1 benzyl chloroformate 
• 80-68-2 DL-threonine 
• 72-19-5 rac-allo-threonine 
• 632-20-2 D-Threonine 
• 24830-94-2 D-allo-threonine 
• 100157-61-7 (D)-allo-threonine hydrochloride 
• 100157-53-7 N-carbobenzyloxy-D-allo-threonine methyl ester 

Downstream Products

• 34660-99-6 O-Trimethylsilyl-N-benzyloxycarbonyl-DL-threonin-trimethylsilylester 
• 78464-34-3 2-(2-Benzyloxycarbonylamino-3-hydroxy-butyrylamino)-3-methyl-but-2-enoic acid ethyl ester 
• 98132-34-4 Z-DL-Thr-DMPir 
• 23161-28-6 N-Carbobenzoxy-DL-threoninaethylester 
• 101890-79-3 2-benzyloxycarbonylamino-acetoacetic acid benzyl ester 
• 16597-50-5 2-benzyloxycarbonylamino-3-hydroxy-butyric acid benzyl ester 
• 16597-50-5 N-benzyloxycarbonyl-DL-threonine benzyl ester 
• 85995-51-3 benzyl N-(benzyloxycarbonyl)-D,L-allothreoninate 
• 122871-70-9 (4R,5S)-5-methyl-2-oxooxazolidine-4-carboxylic acid 
• 1195-19-3 (4R,5R)-5-methyl-2-oxooxazolidine-4-carboxylic acid 
• 1373825-53-6 (3R)-2-benzyloxycarbonylamino-3-(tert-butyldimethylsilyloxy)-butanoic acid 
• 162678-96-8 N-Cbz-D-allo-Threonyl-L-alanine tert-butyl ester 

Relevant articles and documents

One enantiomeric fluorescent sensor pair to discriminate four stereoisomers of threonines

The BINOL-amino alcohol enantiomeric pair (S)-1 and (R)-1 are discovered to conduct both enantioselective and diastereoselective fluorescent discrimination of the four stereoisomers of threonine derivatives. This study utilizes different fluorescence resp

Synthesis and evaluation of in vivo anti-hypothermic effect of all stereoisomers of the thyrotropin-releasing hormone mimetic: Rovatirelin Hydrate

We discovered the orally active thyrotropin-releasing hormone (TRH) mimetic: (4S,5S)-5-methyl-N-{(2S)-1-[(2R)-2-methylpyrrolidin-1-yl]-1-oxo-3-(1,3-thiazol-4-yl)propan-2-yl}-2-oxo-1,3-oxazolidine-4-carboxamide 1 (rovatirelin). The central nervous system (CNS) effect of rovatirelin after intravenous (iv) administration is 100-fold higher than that of TRH. As 1 has four asymmetric carbons in its molecule, there are 16 stereoisomers. We synthesized and evaluated the anti-hypothermic effect of all stereoisomers of 1, which has the (4S),(5S),(2S),(2R) configuration from the N-terminus to the C-terminus, in order to clarify the structure?activity relationship (SAR) of stereoisomers. The (4R),(5R),(2R),(2S)-isomer 16 did not show any anti-hypothermic effect. Only the (4S),(5S),(2S),(2S)-isomer 10, which has the (2S)-2-methylpyrrolidine moiety at the C-terminus showed the anti-hypothermic effect similar to 1. Stereoisomers, which have the (5R) configuration of the oxazolidinone at the N-terminus and the (2R) configuration at the middle-part, showed a much lower anti-hypothermic effect than that of 1. On the other hand, stereoisomers, which have the (4R) configuration of the oxazolidinone at the N-terminus or the (2S) configuration of the C-terminus, have little influence on the anti-hypothermic effect.

CARBAMATE DERIVATIVES OF LACTAM BASED N-ACYLETHANOLAMINE ACID AMIDASE (NAAA) INHIBITORS

Described herein are compounds and pharmaceutical compositions which inhibit N-acylethanolamine acid amidase (NAAA). Described herein are methods for synthesizing the compounds set forth herein and methods for formulating these compounds as pharmaceutical compositions which include these compounds. Also described herein are methods of inhibiting NAAA in order to sustain the levels of palmitoylethanolamide (PEA) and other N-acylethanolamines (NAE) that are substrates for NAAA, in conditions characterized by reduced concentrations of NAE. Also, described here are methods of treating and ameliorating pain, inflammation, inflammatory diseases, and other disorders in which modulation of fatty acid ethanolamides is clinically or therapeutically relevant or in which decreased levels of NAE are associated with the disorder.