246237-03-6

Basic information

• Product Name: 5-[(4-nitrophenyl)methylcarbamoyloxy]-3-hydroxy-3-methylpentanoic acid
• Synonyms: 5-[(4-nitrophenyl)methylcarbamoyloxy]-3-hydroxy-3-methylpentanoic acid
• CAS NO: 246237-03-6
• Molecular Weight: 326.306
• Mol File: 246237-03-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 5-[(4-nitrophenyl)methylcarbamoyloxy]-3-hydroxy-3-methylpentanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[(4-nitrophenyl)methylcarbamoyloxy]-3-hydroxy-3-methylpentanoic acid(246237-03-6)
• EPA Substance Registry System: 5-[(4-nitrophenyl)methylcarbamoyloxy]-3-hydroxy-3-methylpentanoic acid(246237-03-6)

Safety Data

• Hazardous Substances Data: 246237-03-6(Hazardous Substances Data)

Upstream product

• 246237-00-3 methyl-(4-nitro-phenyl)-carbamic acid 3-hydroxy-3-methyl-hex-5-enyl ester 
• 100-15-2 N-methyl(p-nitroaniline) 
• 114580-75-5 (R/S)-3-methyl-5-hexene-1,3-diol 
• 53696-52-9 N-methyl-N-(4-nitrophenyl)carbamoyl chloride 
• 246236-98-6 (4-nitrophenyl)methylcarbamic acid 3-hydroxy-3-methyl-5-oxopentyl ester 

Downstream Products

• 674-26-0 mevalonolactone 

Relevant articles and documents

A catalytic enantioselective route to hydroxy-substituted quaternary carbon centers: Resolution of tertiary aldols with a catalytic antibody

Aldolase antibody 38C2-catalyzed resolutions of tertiary aldols were studied. Tertiary aldols proved to be very good substrates for antibody catalyzed retro-aldol reactions. The catalytic proficiency, (k(cat)/K(M))/k(uncat), of the antibody for these reactions was on the order of 1010 M-1. A fluorogenic tertiary aldol allowed for the quantitative study of enantiomeric excess as a function of reaction conversion, revealing an E value of ca. 160 in this case. Study of a variety of substrates demonstrated that antibody-catalyzed retro-aldolization provides rapid entry to highly enantiomerically enriched tertiary aldols, typically > 95% ee, containing structurally varied, heteroatom-substituted quaternary carbon centers. The utility of this approach to natural product syntheses has been demonstrated with the syntheses of (+)-frontalin, the side chain of Saframycin H, and formal syntheses of (+)- and (-)-mevalonolactone.