70853-26-8

Basic information

• Product Name: (R)-4-methyl-1-oxopentane-2-benzylcarbamate
• Synonyms: (R)-4-methyl-1-oxopentane-2-benzylcarbamate
• CAS NO: 70853-26-8
• Molecular Weight: 249.31
• Mol File: 70853-26-8.mol
• Article Data: 43

Chemical Properties

• CAS DataBase Reference: (R)-4-methyl-1-oxopentane-2-benzylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-4-methyl-1-oxopentane-2-benzylcarbamate(70853-26-8)
• EPA Substance Registry System: (R)-4-methyl-1-oxopentane-2-benzylcarbamate(70853-26-8)

Safety Data

• Hazardous Substances Data: 70853-26-8(Hazardous Substances Data)

Upstream product

• 352535-09-2 benzyl (R)-(1-hydroxy-4-methylpentan-2-yl)carbamate 
• 94202-77-4 ((Z)-(R)-1,5-Dimethyl-hex-2-enylselanyl)-benzene 
• 28862-79-5 Z-D-Leu-OH 
• 94202-81-0 ((E)-(R)-1-Isobutyl-but-2-enyl)-carbamic acid benzyl ester 
• 73397-22-5 Cbz-D-Leu-OMe 
• 2666-93-5 (S)-Leu-OMe 
• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 
• 113283-61-7 benzyl (S)-1-isobutyl-2,2-dimethoxyethylcarbamate 
• 51021-87-5 N-benzyloxycarbonyl-L-leucine methyl ester 
• 501-53-1 benzyl chloroformate 
• 2743-40-0 L-leucine ethyl ester hydrochloride 
• 7533-40-6 (S)-2-amino-4-methylpentan-1-ol 
• 3397-35-1 Z-L-leucine hydroxysuccinimide ester 
• 109075-73-2 benzyl (S)-[1-(N-methoxy-N-methylamino)-4-methyl-1-oxopentan-2-yl]carbamate 

Downstream Products

• 166735-51-9 (+/-)-2-[(Benzyloxycarbonyl)amino]-4-methylpentan-1-ol 
• 113283-61-7 benzyl (S)-1-isobutyl-2,2-dimethoxyethylcarbamate 
• 147298-43-9 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1R,2S)-2-benzyloxycarbonylamino-1-[1-(4-methoxy-benzyloxymethyl)-vinyl]-4-methyl-pentyl ester 
• 111854-80-9 (Z)-(S)-4-Benzyloxycarbonylamino-6-methyl-hept-2-enoic acid methyl ester 
• 132549-28-1 (E)-(S)-4-Benzyloxycarbonylamino-6-methyl-hept-2-enoic acid methyl ester 
• 135691-04-2 ((S)-1-{1-[(Z)-2-Hydroxy-ethylimino]-8-methoxy-isochroman-3-yl}-3-methyl-butyl)-carbamic acid benzyl ester 
• 135691-05-3 ((S)-1-{2-[2-(4,5-Dihydro-oxazol-2-yl)-3-methoxy-phenyl]-1-hydroxy-ethyl}-3-methyl-butyl)-carbamic acid benzyl ester 
• 135691-07-5 (1'R,3S)-3-(1-Benzyloxycarbonylamino-3-methylbutyl)-3,4-dihydro-8-methoxy-1H-2-benzopyran-1-one 
• 135691-06-4 (1'S,3S)-3-(1-Benzyloxycarbonylamino-3-methylbutyl)-3,4-dihydro-8-methoxy-1H-2-benzopyran-1-one 
• 6216-61-1 (S)-(-)-N-(benzyloxycarbonyl)leucinol 
• 137649-68-4 (4-benzyloxycarbonylamino-2,3-dihydroxy-1-isobutyl-6-methyl-heptyl)-carbamic acid benzyl ester 
• 1009587-40-9 (1R,3S,1'S)-1-[1'-[(N-benzyloxycarbonyl)amino]-3'-methyl-butyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester 
• 1009587-37-4 (1S,3S,1'S)-1-[1'-[(N-benzyloxycarbonyl)amino]-3'-methyl-butyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester 

Relevant articles and documents

Probing α-Amino Aldehydes as Weakly Acidic Pronucleophiles: Direct Access to Quaternary α-Amino Aldehydes by an Enantioselective Michael Addition Catalyzed by Br?nsted Bases

The high tendency of α-amino aldehydes to undergo 1,2-additions and their relatively low stability under basic conditions have largely prevented their use as pronucleophiles in the realm of asymmetric catalysis, particularly for the production of quaternary α-amino aldehydes. Herein, it is demonstrated that the chemistry of α-amino aldehydes may be expanded beyond these limits by documenting the first direct α-alkylation of α-branched α-amino aldehydes with nitroolefins. The reaction produces densely functionalized products bearing up to two, quaternary and tertiary, vicinal stereocenters with high diastereo- and enantioselectivity. DFT modeling leads to the proposal that intramolecular hydrogen bonding between the NH group and the carbonyl oxygen atom in the starting α-amino aldehyde is key for reaction stereocontrol.

Discovery of (S)-4-isobutyloxazolidin-2-one as a novel leucyl-tRNA synthetase (LRS)-targeted mTORC1 inhibitor

A series of leucinol analogs were investigated as leucyl-tRNA synthetase-targeted mTORC1 inhibitors. Among them, compound 5, (S)-4-isobutyloxazolidin-2-one, showed the most potent inhibition on the mTORC1 pathway in a concentration-dependent manner. Compound 5 inhibited downstream phosphorylation of mTORC1 by blocking leucine-sensing ability of LRS, without affecting the catalytic activity of LRS. In addition, compound 5 exhibited cytotoxicity against rapamycin-resistant colon cancer cells, suggesting that LRS has the potential to serve as a novel therapeutic target.

Evaluation of transition-state mimics in a superior BACE1 cleavage sequence as peptide-mimetic BACE1 inhibitors

A superior substrate sequence for BACE1 containing transition-state mimics at the scissile site was evaluated as a protease inhibitor. Hydroxymethylcarbonyl (HMC) and hydroxyethylamine (HEA) isosteres were selected as the transition state mimics, and inco