116611-58-6

Basic information

• Product Name: D-Norvaline, N-[(1,1-diMethylethoxy)carbonyl]-, Methyl ester
• Synonyms: D-Norvaline, N-[(1,1-diMethylethoxy)carbonyl]-, Methyl ester;(R)-methyl 2-((tert-butoxycarbonyl)amino)pentanoate;Methyl (2R)-2-{[(tert-butoxy)carbonyl]amino}pentanoate
• CAS NO: 116611-58-6
• Molecular Formula: C₁₁H₂₁NO₄
• Molecular Weight: 231.28874
• Mol File: 116611-58-6.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: D-Norvaline, N-[(1,1-diMethylethoxy)carbonyl]-, Methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: D-Norvaline, N-[(1,1-diMethylethoxy)carbonyl]-, Methyl ester(116611-58-6)
• EPA Substance Registry System: D-Norvaline, N-[(1,1-diMethylethoxy)carbonyl]-, Methyl ester(116611-58-6)

Safety Data

• Hazardous Substances Data: 116611-58-6(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 4184-89-8 methyl (R)-2-(N-acetylamino)pentanoate 
• 142729-70-2 D,L-N-Boc-nor-valine methyl ester 
• 619330-91-5 (R)-methyl 2-aminopentanoate hydrochloride 
• 2013-12-9 D-norvaline 
• 113266-37-8 methyl (Z)-2-((tertbutoxycarbonyl)amino)-2-pentenoate 
• 182495-27-8 (R)-2-tert-Butoxycarbonylamino-pent-3-ynoic acid 
• 173065-20-8 1,1-dimethylethyl (4R)-2,2-dimethyl-4--3-oxazolidine carboxylate 
• 186581-53-3 diazomethane 
• 57521-85-4 N-tert-butoxycarbonyl-D-norvaline 
• 67-56-1 methanol 
• 917-54-4 methyllithium 
• 76969-87-4 tert-Butyloxycarbonyl-L-α-amino-γ-bromobutyric acid methyl ester 
• 182495-17-6 ((R)-1-Hydroxymethyl-but-2-ynyl)-carbamic acid tert-butyl ester 

Downstream Products

• 883559-68-0 tert-butyl (1R,2E,6R,7R,9R)-(10-benzyloxy-6-hydroxy-7,9-dimethyl-8-oxo-1-propyl-dec-2-enyl)-carbamate 
• 883559-62-4 tert-butyl (1R,2Z,6R,7R,9R)-(10-benzyloxy-6-hydroxy-7,9-dimethyl-8-oxo-1-propyl-dec-2-enyl)-carbamate 
• 171560-22-8 (2R)-2-(1,1-dimethylethoxycarbonylamino)pentanal 

Relevant articles and documents

Benzoxaborole Antimalarial Agents. Part 5. Lead Optimization of Novel Amide Pyrazinyloxy Benzoxaboroles and Identification of a Preclinical Candidate

Carboxamide pyrazinyloxy benzoxaboroles were investigated with the goal to identify a molecule with satisfactory antimalarial activity, physicochemical properties, pharmacokinetic profile, in vivo efficacy, and safety profile. This optimization effort discovered 46, which met our target candidate profile. Compound 46 had excellent activity against cultured Plasmodium falciparum, and in vivo against P. falciparum and P. berghei in infected mice. It exhibited good PK properties in mice, rats, and dogs. It was highly active against the other 11 P. falciparum strains, which are mostly resistant to chloroquine and pyrimethamine. The rapid parasite in vitro reduction and in vivo parasite clearance profile of 46 were similar to those of artemisinin and chloroquine, two rapid-acting antimalarials. It was nongenotoxic in an Ames assay, an in vitro micronucleus assay, and an in vivo rat micronucleus assay when dosed orally up to 2000 mg/kg. The combined properties of this novel benzoxaborole support its progression to preclinical development.

Synthesis of enantioenriched aza-proline derivatives through gold(I)-catalyzed cyclization of chiral α-hydrazino esters

A selective gold(I)-catalyzed synthesis of chiral aza-proline derivatives has been developed by ring closure of enantioenriched α-hydrazino esters bearing an alkyne group. These are easily prepared through a synthetic strategy involving two key steps: org

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.