58561-04-9

Basic information

• Product Name: BOC-VAL-OME
• Synonyms: (S)-methyl 2-(tert-butoxycarbonylamino)-3-methylbutanoate;N-t-butoxycarbonyl-L-valine Methyl ester;N-Boc-L-valine Methyl ester, 97%;Methyl N-(tert-butoxycarbonyl)-L-valinate;L-Valine,N-[(1,1-diMethylethoxy)carbonyl]-, Methyl ester;Boc-L-Val-OMe;N-tert-Butoxycarbonylvaline methyl este;BOC-L-VALINE METHYL ESTER
• CAS NO: 58561-04-9
• Molecular Formula: C₁₁H₂₁NO₄
• Molecular Weight: 231.29
• Product Categories: Amino Acid Derivatives;Peptide Synthesis;Valine
• Mol File: 58561-04-9.mol

Chemical Properties

• Melting Point: 194℃
• Boiling Point: 194 °C(lit.)
• Flash Point: 113 °C
• Appearance: /Liquid
• Density: 1.004 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: n20/D 1.44(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 11.13±0.46(Predicted)
• CAS DataBase Reference: BOC-VAL-OME(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-VAL-OME(58561-04-9)
• EPA Substance Registry System: BOC-VAL-OME(58561-04-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 58561-04-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
BOC-VAL-OME is used as an intermediate in the asymmetric synthesis of isoxazoline and hydroxyketomethylene dipeptide isosteres. These compounds are essential in the development of new drugs and therapeutic agents, as they can mimic the structure and function of natural peptides, potentially leading to more effective treatments for various diseases and conditions.
Additionally, BOC-VAL-OME is used to prepare nonsymmetric dihydroxyethylene dipeptide isosteres via epoxyalcohols derived from α-amino acids. These isosteres can be employed in the design of novel bioactive molecules, which may have improved pharmacological properties or reduced side effects compared to existing drugs.

InChI:InChI=1/C11H21NO4/c1-7(2)8(9(13)15-6)12-10(14)16-11(3,4)5/h7-8H,1-6H3,(H,12,14)/t8-/m0/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 134306-34-6 N-(Benzyloxycarbonyl)valine methyl ester 
• 67-56-1 methanol 
• 13734-41-3 N-Boc-(S/R)-valine 
• 5619-05-6 DL-valine methyl ester hydrochloride 
• 74-88-4 methyl iodide 
• 189889-88-1 (2R,5S)-2-(4-Cyanobenzyl)-2,5-dihydro-3,6-dimethoxy-5-isopropylpyrazine 
• 100-36-7 N,N-diethylethylenediamine 
• 395647-19-5 N-{3-[(N,N-dimethylaminophenyl)-4'-diazenyl]benzoyl}-N-tert-butyloxycarbonylvaline methyl ester 
• 58561-04-9 N-Boc-valine methyl ester 
• 4070-48-8 D-Valine methyl ester 

Downstream Products

• 13734-41-3 t-Boc-L-valine 
• 106391-85-9 (R)-methyl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoate 
• 157035-77-3 tert-butyl (S)-(2-hydroxy-2,4-dimethylpentan-3-yl)carbamate 
• 128211-52-9 (3S)-3-N-(tert-butyloxycarbonyl)amino-4-methylpentan-2-one 
• 79069-51-5 (S)-N-tert-butoxycarbonylvalinal 
• 79069-14-0 (S)-2-<(tert-butoxycarbonyl)amino>-3-methylbutan-1-ol 
• 69209-72-9 (N-tert-butoxycarbonyl-L-valyl)-L-valine 
• 108334-64-1 N-tert-butyloxycarbonyl-L-valyl-L-phenylalanine 
• 1105065-38-0 (3S,R(S))-N-(tert-butoxycarbonyl)-3-amino-4-methyl-1-(p-tolylsulfinyl)-2-pentanone 
• 1130247-49-2 (2S)-2-tert-butyloxycarbonylamino-1,1-di(2-methoxy-5-methylphenyl)-3-methyl-1-butanol 
• 1152313-74-0 (S)-2-fluoro-N-(2-hydroxy-2,4-dimethylpentan-3-yl)benzamide 
• 1152313-76-2 (4S)-2-[2-(diphenylphosphino)phenyl]-4,5-dihydro-5,5-dimethyl-4-(1-methylethyl)-oxazole 
• 1152313-77-3 (S)-2-bromo-N-(2-hydroxy-2,4-dimethylpentan-3-yl)benzamide 
• 1152313-75-1 (S)-2-(2-fluorophenyl)-4-isopropyl-5,5-dimethyl-4,5-dihydrooxazole 

Relevant articles and documents

Bioproduction of l-2-Aminobutyric Acid by a Newly-Isolated Strain of Aspergillus tamarii ZJUT ZQ013

Abstract: l-2-Aminobutyric acid (l-ABA), an unnatural amino acid, is a key intermediate of several important drugs. Although some methods have been developed to prepare pure chiral l-ABA, there are still many drawbacks, including low catalytic efficiency, cumbersome steps and high cost due to the addition of some expensive catalysts or coenzymes. Herein, with chemical and biological approaches together, we discovered a newly isolated Aspergillus tamarii ZJUT ZQ013 strain containing a microbial lipase which could be employed to resolve racemic methyl N-Boc-2-aminobutyrate to produce l-ABA with high enantioselectivity (e.e.s?>?99.9%, E = 257). Moreover, the subsequent gram scale experiment confrimed that A. tamarii ZJUT ZQ013 could be an attractive biocatalyst for the efficient preparation of optically pure acid. Graphical Abstract: [Figure not available: see fulltext.]

The effect of substituents on the chiral solvating properties of (S)-1,6-dialkylpiperazine-2,5-diones

The effect of substituents on the chiral solvating properties of 13 different (S)-1,6-dialkylpiperazine-2,5-diones (S)-1a-m and five (3S,6S)-1,3,6-trialkyl analogues (S,S)-1n-r was studied by NMR in CDCl 3 with methyl (RS)-N-benzoylleucinate (R

Enantiomeric resolution of α-amino acid derivatives on two diastereomeric chiral stationary phases based on chiral crown ethers incorporating two different chiral units

Two diastereomeric chiral stationary phases (CSPs) were applied to the liquid chromatographic resolution of various racemic a-amino methyl esters, α-amino N,N-diethylamides and α-amino N-propylamides. The CSP incorporating (R)-3,3' -diphenyl-1,1' -binaphtyl and (R,R)-tartaric acid unit as chiral barriers did not show any chiral recognition. In contrast, the CSP incorporating (R)-3,3'-diphenyl-1,1'-binaphtyl and (S,S)-tartaric acid unit as chiral barriers was found to show excellent chiral recognition especially for the two enantiomers of a-amino N-propylamides. Some of a-amino methyl esters and α-amino N,N-diethylamides were also resolved on the CSP incorporating (R)-3,3'-diphenyl-1,1'-binaphtyl and (S,S)-tartaric acid unit. From these results it was concluded that the two chiral units composing the diastereomeric CSPs can show "matched" or "mismatched" effect on the chiral recognition according to their absolute stereochemistry.

Development of a temporary marker for peptides

3-[(N,N-Dimethylaminophenyl)-4′-diazenyl]benzoic acid was coupled with several amino acid esters and the product acylated further with Boc. The material thus obtained was then submitted to cleavage by electrolysis and nucleophilic attack in order to evaluate the possibility of using this chromophore as a temporary marker.

Direct organo-catalytic asymmetric α-amination of aldehydes - A simple approach to optically active α-amino aldehydes, α-amino alcohols, and α-amino acids

L-Proline as the catalyst: The first direct asymmetric α-amination of aldehydes using L-proline as the catalyst is presented (see scheme; Pg = protecting group). This new reaction gives easy access to optically active α-amino aldehydes, α-amino alcohols, and α-amino acids from simple and easily available starting materials and catalysts. The reactions proceed in high yields and excellent enantioselectivities with as little as 2 mol % of the catalyst.

A temporary marker for biological applications

Having in mind the development of new colour labelled amino acid derivatives, a carboxyl azo dye was coupled to amino acid esters to give the corresponding orange N-acyl derivatives, which were in turn further acylated at their N-terminus with Boc for investigation of the conditions of possible cleavage of the chromophore by electrolysis or with nucleophiles. While difficulties were met with electrolysis owing to competitive reduction of the azo group, cleavage with N,N-diethylaminoethylamine (DEAEA) gave satisfactory results. This allows the use of the chromophore as a temporary marker.

A solid-phase approach to analogues of the antibiotic mureidomycin

A library of 80 analogues of the antibacterial compound mureidomycin was prepared using solid-phase chemistry techniques. (C) 2000 Elsevier Science Ltd.

Stereoselective synthesis of allylic amines by rearrangement of allylic trifluoroacetimidates: Stereoselective synthesis of polyoxamic acid and derivatives of other α-amino acids

On heating in xylene under reflux, allylic trifluoroacetimidates undergo [3,3] sigmatropic rearrangement to regioisomeric allylic trifluoroacetamides. Examples include the rearrangements of the trifluoroacetimidates 16 and 73 to the trifluoroacetamides 17 and 74, which were incorporated into stereoselective syntheses of polyoxamic acid 1, and the rearrangement of the trifluoroacetimidate 26. The rearrangement was the key step in asymmetric syntheses of the (S)- and (R)-valine derivatives 37 and 48. Other examples include rearrangements of the trifluoroacetimidates 52, 54 and 56 prepared from geraniol, cinnamyl alcohol and sorbyl alcohol, respectively, and the more complex trifluoroacetimidates 62 and 69. The stereoselectivity of these rearrangements, which are somewhat faster than rearrangements of analogous allylic trichloroacetimidates, is consistent with the participation of chair-like, six-membered, transition structures. The Royal Society of Chemistry 1999.

ONE-POT CONVERSION OF N-BENZYLOXYCARBONYL GROUP INTO N-TERT-BUTOXYCARBONYL GROUP

An efficient one-pot two stage transformation of the N-Z group into the N-t-Boc group was carried out under neutral conditions.