53308-95-5

Basic information

• Product Name: BOC-NVA-OH
• Synonyms: BOC-NORVALINE;BOC-NHCH[CH3(CH2)2]-COOH;BOC-L-NORVALINE;BOC-L-NVA-OH;BOC-L-2-AMINOVALERIC ACID;BOC-APE(2)-OH;(2S)-2-AMINOPENTANOIC ACID, N-BOC PROTECTED;(2S)-2-[(TERT-BUTOXYCARBONYL)AMINO]PENTANOIC ACID
• CAS NO: 53308-95-5
• Molecular Formula: C₁₀H₁₉NO₄
• Molecular Weight: 217.26
• EINECS: 1533716-785-6
• Product Categories: Aliphatics;Carboxylic Acids;API intermediates;Amino Acids;Norvaline [Nva];Peptide;Carboxylic Acids
• Mol File: 53308-95-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 43-47 °C
• Boiling Point: 357.82°C (rough estimate)
• Flash Point: 164.45 °C
• Appearance: transparent solid
• Density: 1.1518 (rough estimate)
• Vapor Pressure: 8.85E-06mmHg at 25°C
• Refractive Index: 1.4500 (estimate)
• Storage Temp.: 0-6°C
• PKA: 4.02±0.20(Predicted)
• BRN: 3607582
• CAS DataBase Reference: BOC-NVA-OH(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-NVA-OH(53308-95-5)
• EPA Substance Registry System: BOC-NVA-OH(53308-95-5)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 53308-95-5(Hazardous Substances Data)

Usage

Chemical Properties

transparent solid

Uses

BOC-L-Norvaline is used in the synthesis of α-amino acid ester prodrugs used as cytotoxic agents against human lung cancer.

InChI:InChI=1/C10H19NO4/c1-5-6-7(8(12)13)11-9(14)15-10(2,3)4/h7H,5-6H2,1-4H3,(H,11,14)(H,12,13)/p-1/t7-/m0/s1

Upstream product

• 6600-40-4 L-Norvaline 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 116611-57-5 tert-butyl [(1S)-1-(hydroxymethyl)butyl]carbamate 
• 116611-52-0 [(R)-2-Benzenesulfonyl-1-(tetrahydro-pyran-2-yloxymethyl)-butyl]-carbamic acid tert-butyl ester 
• 116611-61-1 ((R)-2-Benzenesulfonyl-1-hydroxymethyl-butyl)-carbamic acid tert-butyl ester 
• 116611-45-1 (2R)-2-t-butoxycarbonylamino-3-phenylsulfonyl-1-(2-tetrahydropyranyloxy)propane 
• 56926-94-4 methyl (2S)-2-[N-(t-butoxycarbonyl)amino]-3-(4-methylbenzenesulfonyl)-oxypropionate 
• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 142729-70-2 D,L-N-Boc-nor-valine methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 116611-44-0 ((R)-2-benzenesulfonyl-1-hydroxymethyl-ethyl)carbamic acid tert-butyl ester 
• 116611-42-8 (R)-2-tert-butoxycarbonylamino-3-phenylsulfanylpropionic acid methyl ester 
• 116611-43-9 (R)-2-tert-butyl carbamoyl-1-hydroxy-3-(phenylthio)propane 

Downstream Products

• 875105-51-4 tert-butyl (1S)-[1-(benzylcarbamoyl)butyl]carbamate 
• 108233-37-0 N-t-BOC-L-Nor-N-hydroxysuccinimide 
• 625122-55-6 tert-butyl (1S)-(1-{[(benzenesulfonyl)amino]carbonyl}butyl)carbamate 
• 64896-37-3 methyl N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-norvalinate 
• 116611-57-5 tert-butyl [(1S)-1-(hydroxymethyl)butyl]carbamate 
• 160801-74-1 (2S)-2-(1,1-dimethylethoxycarbonylamino)pentanal 
• 367268-12-0 C₁₀H₂₀N₂O₃ 
• 794565-04-1 (1-{5-[2-(4-tert-butyl-phenyl)-1-methyl-ethyl]-isoxazol-3-ylcarbamoyl}-butyl)-carbamic acid tert butyl ester 
• 794564-75-3 {1-[5-(4-tert-butyl-phenyl)-isoxazol-3-ylcarbamoyl]-butyl}-carbamic acid tert-butyl ester 
• 794564-77-5 [1-(5-cyclohexyl-isoxazol-3-ylcarbamoyl)-butyl]-carbamic acid tert-butyl ester 
• 859841-46-6 C₂₄H₃₁N₅O₄S 
• 859149-04-5 C₂₇H₃₀FN₃O₆S 

Relevant articles and documents

Microporous Molecular Materials from Dipeptides Containing Non-proteinogenic Residues

Dipeptides with two hydrophobic side chains have proved to be an exceptional source of microporous organic materials, but since previous structures were limited to the incorporation of only proteinogenic residues, their full potential as adsorbents has remained unexplored. Single-crystal XRD data for ten new compounds with non-proteinogenic L-2-aminobutanoic acid and/or L-2-amino-pentanoic acid are presented. The gas-phase accessibility of their crystal pores, with cross-sections of 2.3 to 5.1?, was monitored by CO2 and CH4 adsorption isotherms. Included CO2 was also detected spectroscopically by 2D MAS NMR. An extensive conformational analysis reveals that the use of linear rather than branched side chains (such as L-valine and L-isoleucine) affords peptides with a greater degree of conformational freedom and yields more-flexible channel surfaces that may easily adapt to a series of potential guest molecules.

Enzymatic approach to both enantiomers of N-Boc hydrophobic amino acids

Protease catalysed hydrolysis of N-Boc-amino acid esters allows us to obtain N-Boc l-acids and d-esters of amino butanoic acid, nor-leucine, nor-valine, leucine and t-leucine in excellent ee. The reaction occurs in short reaction times and high concentrations. When a biphasic system (buffer-MTBE) is employed, a strong solvent effect is observed. This method could be of significance for the preparation of d-t-leucine, for which a practical method is currently unavailable.

Synthesis of new indolactam analogues by microbial conversion

Ten indolactam congeners with L-Ala, Abu, γ,δ-Δ-Nva, Nva, Nle, tert-Leu, Leu, Ile, allo-Ile. Phg instead ofL-Val in (-)-indolactam-Val, were synthesized from their seco-compounds (N-methyl-L-amino acidyl-L-tryptophonol) by microbial conversion.