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

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

Uses

Used in Biochemistry and Pharmaceutical Research:
H-THR(BZL)-OH is used as a building block in solid-phase peptide synthesis for the creation of complex peptides and proteins. The presence of the benzoyl group allows for specific chemical reactions and modifications, enhancing its utility in research and development.
Used in Protein and Antibody Synthesis:
As threonine is an essential amino acid involved in protein synthesis, H-THR(BZL)-OH contributes to the formation of proteins and antibodies, which are crucial for various biological functions and therapeutic applications.
Used in Collagen and Elastin Formation:
H-THR(BZL)-OH plays a role in the synthesis of collagen and elastin, which are vital structural proteins in the body responsible for maintaining skin elasticity, tissue integrity, and providing support to various organs.

Upstream product

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

Downstream Products

• 15260-10-3 N-Boc-O-benzyl-L-threonine 
• 72-19-5 L-threonine 
• 73535-45-2 (2S,3R)-2-acetamido-3-benzyloxybutanoic acid 
• 669738-91-4 (2S,3R)-3-(benzyloxy)-2-hydroxybutanoic acid 
• 173987-06-9 N-tert-butoxycarbonyl-O-benzyl-D-allo-threonine 
• 186826-26-6 Thr(Bzl) 
• 188660-10-8 4-((R)-1-Benzyloxy-ethyl)-2-methyl-4H-oxazol-5-one 
• 186826-19-7 (2R,3R)-2-Acetylamino-3-benzyloxy-butyric acid 
• 90072-35-8 (2S,3R)-O-benzyl-threonine methyl ester 
• 1638884-69-1 N-(phenoxycarbonyl)-O-benzyl-L-threonine 
• 101655-20-3 4-(1-benzyloxy-ethyl)-oxazolidine-2,5-dione 
• 72-19-5 rac-allo-threonine 
• 462117-82-4 C₅₉H₈₃N₇O₁₅ 
• 462117-84-6 C₅₉H₈₂N₆O₁₆ 

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.

Facile synthesis of α-hydroxy carboxylic acids from the corresponding α-amino acids

An effective and improved procedure is developed for the synthesis of α-hydroxy carboxylic acids by treatment of the corresponding protonated α-amino acid with tert-butyl nitrite in 1,4-dioxane-water. The amino moiety must be protonated and located α to a carboxylic acid function in order to undergo initial diazotization and successive hydroxylation, since neither β-amino acids nor acid derivatives such as esters and amides undergo hydroxylations. The method is successfully applied for the synthesis of 18 proteinogenic amino acids.

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.

2,2-Difluoro-1,3,2-oxazaborolidin-5-ones: Novel approach for selective side-chain protection of serine and threonine

2,2-Difluoro-1,3,2-oxazaborolidin-5-ones 1, which are synthesized from BF3 and salts of amino acids, are highly effective, convenient and, moreover, inexpensive intermediates for the simultaneous protection of both α-amino and α-carboxy groups in α-amino acids. The new method streamlines the hitherto tedious procedures for side-chain protection of Ser and Thr. Ser(Bu′), Thr(Bu′), Ser(Bzl) and Thr(Bzl) are obtained by this procedure in high yields and in pure form using highly reactive reagents.

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.

Acceleration of the N(α)-deprotection rate by the addition of m-cresol to diluted methanesulfonic acid and its application to the Z(OMe)-based solid-phase syntheses of human pancreastatin-29 and magainin 1

In solid-phase peptide synthesis, the addition of m-cresol to diluted methanesulfonic acid (MSA) in dichloromethane accelerated the deprotection rate of the acid-labile α-amino protecting group, the p-methoxybenzyloxycarbonyl (Z(OMe)) group. Further, 0.1 M MSA, 20% m-cresol/CH2Cl2 was found to be a practically useful N(α)-deprotecting reagent system, since the deprotection of the Z(OMe) group occurred selectively within 30 min at room temperature, leaving intact the other side chain protecting groups, such as benzyloxycarbonyl, benzyl ester, S-p-methoxybenzyl and N(G)-mesitylene-2-sulfonyl groups. This reagent system was applied to the Z(OMe)-based solid phase syntheses of human pancreastatin-29 and magainin 1.

A NEW SYNTHESIS OF O-BENZYL-L-THREONINE

O-Benzyl-L-threonine can be prepared in a one-pot synthesis in 80percent yield by using ethyl acetoacetate to protect the α-amino group, followed by treatment with benzyl bromide and removal of the N-protecting group under acidic conditions.