22838-58-0

Basic information

• Product Name: Boc-D-Valine
• Synonyms: N-Boc-D-valine, 98+%;BOC-D-VALINE extrapure;BOC-D-VALINE, 98+%;N-a-t-Boc-D-valine;N-t-Boc-D-valine;t-Butoxycarbonyl-D-va;S-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic aci;N-Boc-D-valine Boc-D-Val-OH
• CAS NO: 22838-58-0
• Molecular Formula: C₁₀H₁₉NO₄
• Molecular Weight: 217.26
• EINECS: 1533716-785-6
• Product Categories: Amino Acids;Valine [Val, V];Boc-Amino Acids and Derivative;Amino Acids (N-Protected);Biochemistry;Boc-Amino Acids;Boc-Amino acid series;Amino Acid Derivatives
• Mol File: 22838-58-0.mol
• Article Data: 19

Chemical Properties

• Melting Point: 164-165 °C
• Boiling Point: 357.82°C (rough estimate)
• Flash Point: 160.542 °C
• Appearance: white to off-white powder
• Density: 1.1518 (rough estimate)
• Vapor Pressure: 1.42E-05mmHg at 25°C
• Refractive Index: 6 ° (C=1, AcOH)
• Storage Temp.: 0-6°C
• Solubility: DMSO, Methanol
• PKA: 4.01±0.10(Predicted)
• BRN: 2050408
• CAS DataBase Reference: Boc-D-Valine(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-D-Valine(22838-58-0)
• EPA Substance Registry System: Boc-D-Valine(22838-58-0)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 22838-58-0(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

Uses

tert-Butoxycarbonyl-D-valine is used in the preparation of selective CCR1 antagonists in the treatment of rheumatoid arthritis. Also used in the preparation of antileishmanial agents.

InChI:InChI=1/C10H19NO4/c1-6(2)7(8(12)13)11-9(14)15-10(3,4)5/h6-7H,1-5H3,(H,11,14)(H,12,13)/p-1/t7-/m1/s1

Upstream product

• 4530-20-5 BOC-glycine 
• 640-68-6 D-Val-OH 
• 24424-99-5 di-tert-butyl dicarbonate 
• 60079-03-0 p-nitrophenyl-N-(t-butoxycarbonyl)-D-valinate 
• 117049-11-3 2-tert-Butoxycarbonylamino-3-methyl-butyric acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 117049-08-8 (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl<(tert-butoxycarbonyl)amino>bromoacetate 
• 117681-86-4 (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl (tert-butoxycarbonyl)aminoacetate 
• 111652-06-3 tert-butyl (tert-butoxycarbonyl)valinate 
• 516-06-3 D,L-valine 
• 89037-64-9 1-tert-butoxycarbonyloxybenzotriazole 
• 169556-48-3 rac-tert-butyl (1-hydroxy-3-methylbutan-2-yl)carbamate 
• 75-30-9 2-iodo-propane 

Downstream Products

• 84559-70-6 N^α-(t-butoxycarbonyl)-D-valylleucine benzyl ester 
• 96935-51-2 Boc-D-Val-Orn(Z)-OEt 
• 96935-56-7 Boc-D-Val-Orn(Z)-Leu-Phe-Pro-OBzl 
• 104944-35-6 (R)-2-tert-Butoxycarbonylamino-3-methyl-butyric acid (bis-benzhydryloxy-phosphoryl)-phenyl-methyl ester 
• 104944-35-6 (R)-2-tert-Butoxycarbonylamino-3-methyl-butyric acid (R)-(bis-benzhydryloxy-phosphoryl)-phenyl-methyl ester 
• 153346-65-7 Boc-D-Val-N-MeArg(Tos)-Gly-OBzl 
• 109880-47-9 (R)-2-tert-Butoxycarbonylamino-3-methyl-butyric acid (R)-1-(2-oxo-2-phenyl-ethoxycarbonyl)-ethyl ester 
• 70717-76-9 (R)-(1-carbamoyl-2-methyl-propyl)-carbamicacidtert-butyl ester 
• 279255-85-5 (R)-O-benzyl 2-N-(t-butoxycarbonyl)amino-3-methylbutanoate 
• 13850-91-4 (R)-2-(tert-butoxycarbonyl(methyl)amino)-3-methylbutanoic acid 
• 33419-01-1 H-Val-OH p-toluenesulfonic acid salt 
• 116480-86-5 (S)-2-((R)-2-tert-Butoxycarbonylamino-3-methyl-butyrylamino)-3-phenyl-propionic acid 
• 936627-94-0 (+)-(R)-N²-(tert-butoxycarbonyl)-N¹-(4-chloro-2,6-dimethylphenyl)valinamide 

Relevant articles and documents

A Facile Approach to the Synthesis of Benzothiazoles from N-Protected Amino Acids

Abstract: –A simple trituration method for the synthesis of 2-substituted benzothiazoles derived from N-protected amino acids and 2-aminothiophenol using molecular iodine as a mild Lewis acid catalyst has been proposed. The reaction occurs in one step for 20–25 min in solve-free conditions and provides the target products in excellent yields.

Amino acid conjugated antimicrobial drugs: Synthesis, lipophilicity- activity relationship, antibacterial and urease inhibition activity

Present work describes the in vitro antibacterial evaluation of some new amino acid conjugated antimicrobial drugs. Structural modification was attempted on the three existing antimicrobial pharmaceuticals namely trimethoprim, metronidazole, isoniazid. Twenty one compounds from seven series of conjugates of these drugs were synthesized by coupling with some selected Boc-protected amino acids. The effect of structural features and lipophilicity on the antibacterial activity was investigated. The synthesized compounds were evaluated against five standard American type culture collection (ATCC) i.e. Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa and Salmonella typhi strains of bacteria. Our results identified a close relationship between the lipophilicity and the activity. Triazine skeleton proved beneficial for the increase in hydrophobicity and potency. Compounds with greater hydrophobicity have shown excellent activities against Gram-negative strains of bacteria than Gram-positive. 4-amino unsubstituted trimethoprim-triazine derivative 7b have shown superior activity with MIC = 3.4 μM (2 μg/mL) for S. aureus and 1.1 μM (0.66 μg/mL) for E. coli. The synthesized compounds were also evaluated for their urease inhibition study. Microbial urease from Bacillus pasteurii was chosen for this study. Triazine derivative 7a showed excellent inhibition with IC50 = 6.23 ± 0.09 μM. Docking studies on the crystal structure of B. pasteurii urease (PDB ID 4UBP) were carried out.

Chemo- and Diastereoselective N-Heterocyclic Carbene-Catalyzed Cross-Benzoin Reactions Using N-Boc-α-amino Aldehydes

N-Boc-α-amino aldehydes are shown to be excellent partners in cross-benzoin reactions with aliphatic or heteroaromatic aldehydes. The chemoselectivity of the reaction and the facial selectivity on the amino aldehyde allow cross-benzoin products to be obtained in good yields and good diastereomeric ratios. The developed method is utilized as the key step in a concise total synthesis of d-arabino-phytosphingosine.