4378-10-3

Basic information

• Product Name: H-THR(BZL)-OH
• Synonyms: O-BENZYL-L-THREININE;O-BENZYL-L-THREONINE;L-THREONINE BENZYL ESTER;H-THR(BZL)-OH;H-L-THR(BZL)-OH;O-BENZYL-L-THREONINE HCL;H-Thr-Obzl.HCl;(2S,3R)-2-AMINO-3-BENZYLOXYBUTANOIC ACID
• CAS NO: 4378-10-3
• Molecular Formula: C₁₁H₁₅NO₃
• Molecular Weight: 209.24
• Product Categories: Amino Acids and Derivatives;A - HPeptide Synthesis;Amino Acid Derivatives;Amino Acids;Modified Amino Acids;Threonine
• Mol File: 4378-10-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 197 °C (decomp)(Solv: water (7732-18-5))
• Boiling Point: 362.9±37.0 °C(Predicted)
• Appearance: /
• Density: 1.180±0.06 g/cm3(Predicted)
• Storage Temp.: Store at RT.
• PKA: 2.13±0.10(Predicted)
• CAS DataBase Reference: H-THR(BZL)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: H-THR(BZL)-OH(4378-10-3)
• EPA Substance Registry System: H-THR(BZL)-OH(4378-10-3)

Safety Data

• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 4378-10-3(Hazardous Substances Data)

Usage

General Description

H-THR(BZL)-OH is a chemical compound that is composed of the amino acid threonine (THR) bound to a benzoyl (BZL) group, which is a derivative of benzoyl chloride. H-THR(BZL)-OH is commonly used in solid-phase peptide synthesis as a building block to create complex peptides and proteins. Threonine is an essential amino acid that plays a key role in protein and antibody synthesis, as well as in the formation of collagen and elastin in the body. The addition of the benzoyl group to threonine allows for specific chemical reactions and modifications to be carried out, making it a valuable tool in the field of biochemistry and pharmaceutical research.

Upstream product

• 69863-36-1 N-benzyloxycarbonyl-O-benzyl-L-threonine 
• 100-39-0 benzyl bromide 
• 15260-10-3 N-Boc-O-benzyl-L-threonine 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 75444-38-1 Threonine mono sodium salt 

Downstream Products

• 15260-10-3 N-Boc-O-benzyl-L-threonine 
• 72-19-5 L-threonine 
• 1638884-69-1 N-(phenoxycarbonyl)-O-benzyl-L-threonine 
• 90072-35-8 (2S,3R)-O-benzyl-threonine methyl ester 
• 186826-19-7 (2R,3R)-2-Acetylamino-3-benzyloxy-butyric acid 
• 188660-10-8 4-((R)-1-Benzyloxy-ethyl)-2-methyl-4H-oxazol-5-one 
• 186826-26-6 Thr(Bzl) 
• 173987-06-9 N-tert-butoxycarbonyl-O-benzyl-D-allo-threonine 
• 462117-82-4 C₅₉H₈₃N₇O₁₅ 
• 462117-84-6 C₅₉H₈₂N₆O₁₆ 
• 462117-74-4 (S)-1-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-4-methyl-pentanoyl}-pyrrolidine-2-carboxylic acid (1S,2R)-2-benzyloxy-1-benzyloxycarbonyl-propyl ester 
• 462117-75-5 (S)-1-{(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionyloxy]-4-methyl-pentanoyl}-pyrrolidine-2-carboxylic acid (1S,2R)-2-benzyloxy-1-benzyloxycarbonyl-propyl ester 
• 462117-87-9 (S)-1-{(S)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-4-methyl-pentanoyl}-pyrrolidine-2-carboxylic acid (1S,2R)-2-benzyloxy-1-benzyloxycarbonyl-propyl ester 
• 462117-88-0 (S)-1-{(S)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionyloxy]-4-methyl-pentanoyl}-pyrrolidine-2-carboxylic acid (1S,2R)-2-benzyloxy-1-benzyloxycarbonyl-propyl ester 

Relevant articles and documents

Bifunctional aryloxyphosphoramidate prodrugs of 2′-: C -Me-uridine: Synthesis and anti-HCV activity

In an attempt to identify novel nucleoside phosphoramidate analogues for improving the anti-HCV activity of 2′-C-Me-uridine, we have synthesized for the first time a series of l-glutamic acid, l-serine, l-threonine and l-tyrosine containing aryloxyphosphoramidate prodrugs of 2′-C-Me-uridine. Evaluation of their activity against HCV revealed that they displayed very potent anti-HCV activity, with EC50 values that are in the same range as of Sofosbuvir.

A novel type of Pd/C-catalyzed hydrogenation using a catalyst poison: Chemoselective inhibition of the hydrogenolysis for O-benzyl protective group by the addition of a nitrogen-containing base

A mild and chemoselective hydrogenation method for a variety of reducible functional groups distinguishing front aliphatic and aromatic' benzyl ethers was accomplished by the addition of an appropriate nitrogen- containing base to the Pd/C-catalyzed hydrogenation system.

Selective Inhibition of Benzyl Ether Hydrogenolysis with Pd/C Due to the Presence of Ammonia, Pyridine or Ammonium Acetate

Ammonia, pyridine and ammonium acetate were found to be extremely effective as inhibitors of Pd/C catalyzed benzyl ether hydrogenolysis.While olefin, Cbz, benzyl ester and azide functionalities were hydrogenated smoothly, benzyl ethers were not cleaved in the presence of these additives.