15260-10-3

Usage

Uses

Used in Pharmaceutical Industry:
Boc-O-Benzyl-L-threonine is used as a key building block for the synthesis of peptides, which are essential in the development of various pharmaceutical products. The growing peptide drug market highlights the importance of fast and reliable peptide synthesis, making this amino acid derivative a valuable component in the industry.
Used in Research and Development:
In the realm of research and development, Boc-O-Benzyl-L-threonine is utilized for the creation and modification of peptides with specific properties and functions. Its versatility as a building block allows scientists to explore new avenues in drug discovery and therapeutic applications.
Used in Drug Delivery Systems:
Boc-O-Benzyl-L-threonine can also be employed in the design and development of drug delivery systems, where its unique properties can be harnessed to improve the efficacy and targeted delivery of peptide-based drugs.
Overall, Boc-O-Benzyl-L-threonine is a versatile and essential component in the pharmaceutical and biotechnology industries, playing a critical role in the synthesis of peptides and the advancement of peptide-based therapies.

InChI:InChI=1/C9H17NO5/c1-5(11)6(7(12)13)10-8(14)15-9(2,3)4/h5-6,11H,1-4H3,(H,10,14)(H,12,13)/t5-,6+/m1/s1

Synthetic route

Boc-Thr-OH (2592-18-9) + benzyl bromide (100-39-0) → N-Boc-O-benzyl-L-threonine (15260-10-3)

Conditions	Yield
Stage #1: Boc-Thr-OH With sodium hydride In N,N-dimethyl-formamide; mineral oil at -20℃; for 2h; Inert atmosphere; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 20 - 25℃; for 3h;	90%
Stage #1: Boc-Thr-OH With sodium hydride In N,N-dimethyl-formamide at -20℃; for 2h; Inert atmosphere; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere;	80%
Stage #1: Boc-Thr-OH With sodium hydride In N,N-dimethyl-formamide at -20℃; for 2h; Inert atmosphere; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 12h; Time;	71%

N-Boc-Thr(OBn)-PAM resin → N-Boc-O-benzyl-L-threonine (15260-10-3)

Conditions	Yield
With trimethyltin(IV) hydroxide In 1,2-dichloro-ethane for 9h; Heating;	90%

(2S,3R)-3-Benzyloxy-2-tert-butoxycarbonylamino-butyric acid 2-trimethylsilanyl-ethoxymethyl ester (185461-75-0) → N-Boc-O-benzyl-L-threonine (15260-10-3)

Conditions	Yield
With magnesium bromide In dichloromethane for 3h; Ambient temperature; addition at -20 deg C, 0.5 h;	83%

Upstream product

• 4378-10-3 O-benzyl-L-threonine 
• 98015-52-2 1,2,2,2-Tetrachloroethyl tert-Butyl Carbonate 
• 2592-18-9 Boc-Thr-OH 
• 100-39-0 benzyl bromide 
• 185461-75-0 (2S,3R)-3-Benzyloxy-2-tert-butoxycarbonylamino-butyric acid 2-trimethylsilanyl-ethoxymethyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 100-44-7 benzyl chloride 

Downstream Products

• 70707-56-1 Boc-Thr(CH₂Ph)-Cys(CH₂Ph)-OMe 
• 40162-62-7 BOC-Thr(Bn)-Phe-OMe 
• 76398-76-0 N-(t-butoxycarbonyl)-O-benzyl-L-threonine N-hydroxy-5-norbornene-2,3-dicarboximide ester 
• 135077-21-3 N^α-tert-butoxycarbonyl-O-benzyl-threonyl-N^ε-benzyloxycarbonyl-lysine benzyl ester 
• 124-38-9 carbon dioxide 
• 126045-65-6 (4S,5R)-5-Benzyloxy-4-tert-butoxycarbonylamino-3-oxo-hexanoic acid 4-nitro-benzyl ester 
• 76369-98-7 Boc-Thr(Bzl)-Pro-OPic 
• 118171-84-9 Boc-(S)-Thr(Bzl)-(3S,4R,5S)-Ist-OTce 
• 76369-79-4 Boc-Thr(Bzl)-Pro-Lys(Pipoc)-Ala-OPic 
• 94805-95-5 Boc-L-Thr(Bzl)-L-Ser(Bzl)-L-Dpr(Z)-OBzl 
• 63076-44-8 N-tert-butoxycarbonyl-L-threonine N-hydroxysuccinimide ester 
• 123621-81-8 Boc-Thr(OBn)-Gly-Ser(OBn)-NHCH₃ 
• 122895-46-9 (2S,3R)-3-Benzyloxy-2-tert-butoxycarbonylamino-butyric acid 2-(4-phenylazo-benzenesulfonyl)-ethyl ester 
• 109277-03-4 N-t-butoxycarbonyl-O-benzyl-L-threonyl-N^ε-benzyloxycarbonyl-L-lysyl-L-prolyl-N^ω-nitro-L-arginine 4-picolyl ester 

Relevant academic research and scientific papers

Synthesis of the Tripeptides Tyr-Thr-Lys Phosphorylated with Isopropyl Methyl- and (Deuteromethyl)phosphonochloridates as Reference Standards for the Analysis of Biomedical Samples

A procedure for the phosphorylation of the tripeptide Tyr-Thr-Lys with isopropyl methyl- or (deuteromethyl)phosphonochloridate is developed. The phosphorylated tripeptides are intended for use as reference standards in the analysis of blood samples of people suspected to have been exposed to acetylcholinesterase inhibitors. Conditions of hromatographic separation and purification of the synthesized compounds are determined and optimized, which ensures the preparation of high-purity phosphorylated tripeptides.

SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF

Disclosed are compounds having potency in the modulation of NMDA receptor activity. Such compounds can be used in the treatment of conditions such as depression and related disorders. Orally delivered formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.

OXABOROLE ESTERS AND USES THEREOF

The present invention provides oxaborole ester compounds and compositions thereof which are useful to treat diseases associated with parasites, such as Chagas Disease and African Animal Trypanosomosis.

SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF

Disclosed are compounds having enhanced potency in the modulation of NMDA receptor activity. Such compounds are contemplated for use in the treatment of conditions such as depression and related disorders. Orally available formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed. Formula (I).

SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF

Disclosed are compounds having enhanced potency in the modulation of NMDA receptor activity. Such compounds are contemplated for use in the treatment of conditions such as depression and related disorders. Orally available formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.

SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF

Disclosed are compounds having enhanced potency in the modulation of NMD A receptor activity. Such compounds are contemplated for use in the treatment of conditions such as depression and related disorders. Orally available formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.

Fatty acid analogs and prodrugs

Novel derivatives of fatty acid analogs that have from one to three heteroatoms in the fatty acid moiety which can be oxygen, sulfur or nitrogen, are disclosed in which the carboxy-terminus has been modified to form various amides, esters, ketones, alcohols, alcohol esters and nitrites thereof. These compounds are useful as substrates for N-myristoyltransferase (NMT) and/or its acyl coenzyme, and as anti-viral and anti-fungal agents or pro-drugs of such agents. Illustrative of the disclosed compounds are fatty acid amino acid analogs of the structure STR1 in which x is the ethyl or t-butyl ester of an amino acid such as Gly, L-Ala, L-Ile, L-Phe, L-Trp, L-Thr or an amide such as NHCH2 C6 H5 or NH(CH2)2 C6 H5.

Selective detachment of Boc-protected amino acids and peptides from Merrifield, PAM and Wang resins by trimethyltin hydroxide

We describe the development of a new non-acidolytic and non- nucleophilic method for the selective cleavage by trimethyltin hydroxide of amino acids and dipeptides at benzyl ester links attached to resins commonly used in peptide synthesis.

Mild, selective cleavage of amino acid and peptide β-(trimethylsilyl)ethoxymethyl (SEM) esters by magnesium bromide

Magnesium bromide etherate has been previously shown to cleave β-(trimethylsilyl)ethoxymethyl (SEM) esters of aliphatic acids. This methodology has now been extended to amino acid and peptide derivatives in the presence of protecting groups typically encountered in peptide chemistry, including the Boc, Cbz, Fmoc and Troc carbamates as well as benzyl-, tert-butyl- and tert-butyldimethylsilyl ethers. The stability of fluoride sensitive protecting groups to magnesium bromide allows for added selectivity in the removal of SEM esters in organic synthesis.

Fatty acid analogs and prodrugs

Novel derivatives of fatty acid analogs that have from one to three heteroatoms in the fatty acid moiety which can be oxygen, sulfur or nitrogen, are disclosed in which the carboxy-terminus has been modified to form various amides, esters, ketones, alcohols, alcohol esters and nitriles thereof. These compounds are useful as substrates for N-myristoyltransferase (NMT) and/or its acyl coenzyme, and as anti-viral and anti-fungal agents or pro-drugs of such agents. Illustrative of the disclosed compounds are fatty acid amino acid analogs of the structure STR1 in which X is the ethyl or t-butyl ester of an amino acid such as Gly, L--Ala, L--Ile, L--Phe, L--Trp, L--Thr or an amide such as NHCH2 C6 H5 or NH(CH2)2 C6 H5,