147471-66-7

Basic information

• Product Name: (S)-4-tert-Butoxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester
• Synonyms: (S)-4-tert-Butoxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester
• CAS NO: 147471-66-7
• Molecular Weight: 409.436
• Mol File: 147471-66-7.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: (S)-4-tert-Butoxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-tert-Butoxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester(147471-66-7)
• EPA Substance Registry System: (S)-4-tert-Butoxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester(147471-66-7)

Safety Data

• Hazardous Substances Data: 147471-66-7(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 1676-73-9 L-glutamic acid γ-benzyl ester 
• 13574-13-5 Boc-Glu(OBzl)-OH 
• 541-41-3 chloroformic acid ethyl ester 

Downstream Products

• 73984-00-6 N-t-Butoxycarbonyl-γ-benzyl-L-glutamyl-γ-benzyl-L-glutamyl-O-benzyl-L-seryl-L-leucyl-L-alanine benzyl ester 
• 73984-02-8 N-t-Butoxycarbonyl-β-benzyl-L-aspartyl-γ-benzyl-L-glutamyl-γ-benzyl-L-glutamyl-O-benzyl-L-seryl-L-leucyl-L-alanine benzyl ester 
• 1237501-83-5 Boc-Glu(Bzl)-CH₂N₃ 
• 1237502-01-0 C₂₁H₂₆N₄O₇ 
• 1237501-68-6 benzyl (S)-6-bromo-4-((tert-butoxycarbonyl)amino)-5-oxohexanoate 
• 190586-72-2 N-tert-butoxycarbonyl-L-seryl-L-glutamic acid 1-methylamide 5-benzyl ester 
• 190586-78-8 N-tert-butoxycarbonyl-D-seryl-L-glutamic acid 1-methylamide 5-benzyl ester 
• 190587-50-9 -L-glutamic acid 1-methylamide 5-benzyl ester 
• 190587-46-3 (S)-4-Methylcarbamoyl-4-[(S)-2-(2-tetradecyl-hexadecanoylamino)-3-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propionylamino]-butyric acid benzyl ester 
• 190587-44-1 -L-glutamic acid 1-methylamide 5-benzyl ester 
• 190587-42-9 N-(tert-butoxycarbonyl)-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-L-seryl-L-glutamic acid 1-methylamide 5-benzyl ester 
• 190587-51-0 (S)-4-[(R)-2-Amino-3-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propionylamino]-4-methylcarbamoyl-butyric acid benzyl ester 
• 190587-47-4 (S)-4-[(S)-2-Amino-3-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propionylamino]-4-methylcarbamoyl-butyric acid benzyl ester 
• 82594-35-2 (S)-4-Amino-4-methylcarbamoyl-butyric acid benzyl ester 

Relevant articles and documents

Hydrogen bond surrogate stabilized water soluble 310-helix from a disordered pentapeptide containing coded α-amino acids

Replacing a hypothetical i + 3 → i peptide H-bond in a disordered pentapeptide, that lacks any helicogenic Cα-tetrasubstituted residues, with a propyl linker and carbamylating the N-terminal nitrogen constrains it in the elusive 310-helical structure with high helicity and stability under varying conditions of temperature and pH, confirmed by NMR and CD analyses.

CuI-promoted one-pot synthesis of N-boc protected β-ketotriazole amino acids: Application in the synthesis of new class of dipeptidomimetics

One-pot click chemistry of Nα-Boc-bromomethylketones, NaN3 and propiolic acid affords N-Boc protected 1,4- disubstituted 1,2,3-β-ketotriazole acids in good to excellent yield. The use of CuI as catalyst and DMSO as solvent leads the click react

Potent and fully noncompetitive peptidomimetic inhibitor of multidrug resistance P-glycoprotein

Nα-Boc-l-Asp(OBn)-l-Lys(Z)-OtBu (reversin 121, 1), an inhibitor of the P-gp ABC transporter, was used to conceive compounds inhibiting the drug efflux occurring through the Hoechst 33342 and daunorubicin transport sites of P-gp, respectively H and R sites. Replacement of the aspartyl residue by trans-4-hydroxy-l-proline (4(R)Hyp) gave compounds 11 and 15 characterized by half-maximal inhibitory concentrations (IC50) of 0.6 and 0.2 μM, which are 2-and 7-fold lower than that of the parent molecule. The difference in IC50 between 11 and 15 rests on the carbonyl group of the peptidyl bond, reduced in 15. Those compounds are rather specific of P-gp, having no or limited activity on MRP1 and BCRP. 15 displayed no marked cytotoxicity up to 10-fold its IC50. Importantly, 15 equally inhibited the Hoechst 33342 and daunorubicin effluxes through a typical noncompetitive inhibition mechanism, suggesting its binding to a site different from the H and R drug-transport sites.