88319-44-2

Basic information

• Product Name: L-Leucine, 4-methyl-N-[(phenylmethoxy)carbonyl]-
• CAS NO: 88319-44-2
• Molecular Formula: C15H21NO4
• Molecular Weight: 279.336
• Mol File: 88319-44-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: L-Leucine, 4-methyl-N-[(phenylmethoxy)carbonyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: L-Leucine, 4-methyl-N-[(phenylmethoxy)carbonyl]-(88319-44-2)
• EPA Substance Registry System: L-Leucine, 4-methyl-N-[(phenylmethoxy)carbonyl]-(88319-44-2)

Safety Data

• Hazardous Substances Data: 88319-44-2(Hazardous Substances Data)

Upstream product

• 57224-50-7 (S)-2-Amino-4,4-dimethyl-pentanoic acid 
• 501-53-1 benzyl chloroformate 
• 26054-60-4 ((S)-2-Oxo-oxetan-3-yl)-carbamic acid benzyl ester 
• 594-19-4 tert.-butyl lithium 
• 88319-39-5 2-carbamoyl-4,4-dimethylpentanoic acid 
• 479353-90-7 2-amino-4,4-dimethyl-pentanenitrile 
• 60122-72-7 4,4-Dimethyl-2(R)-aminopentanoic acid 
• 88319-38-4 2-cyano-4,4-dimethylpentanoic acid 
• 7065-46-5 3,3-dimethylbutanoic acid chloride 
• 2987-16-8 3,3-dimethylbutyrylaldehyde 
• 39168-28-0 (E)-2-cyano-4,4-dimethyl-pent-2-enoic acid 
• 57224-50-7 L-neopentylglycine 
• 88319-40-8 N-formyl-L-neopentylglycine 

Downstream Products

• 890088-95-6 2(S)-benzyloxycarbonylamino-4,4-dimethylpentanoic acid 3-methyloxetan-3-ylmethyl ester 
• 769964-71-8 (S)-3-((S)-2-Benzyloxycarbonylamino-4,4-dimethyl-pentanoylamino)-4-(5-fluoro-2,3-dihydro-indol-1-yl)-butyric acid tert-butyl ester 

Relevant articles and documents

HALOALKYL CONTAINING COMPOUNDS AS CYSTEINE PROTEASE INHIBITORS

The present invention is directed to compounds that are inhibitors of cysteine proteases, in particular, cathepsins B, K, L, F, and S and are therefore useful in treating diseases mediated by these proteases. The present invention is directed to pharmaceutical compositions comprising these compounds and processes for preparing them.

Protease inhibitors

The present invention provides bis-aminomethylcarbonyl compounds that are inhibitors of cysteine and serine proteases. The compounds are particularly useful for treating diseases in which excess cysteine protease activity has been implicated, including osteoporosis, periodontitis and arthritis.

Conversion of Serine β-Lactones to Chiral α-Amino Acids by Copper-Containing Organolithium and Organomagnesium Reagents

A method for the synthesis of optically pure α-amino acids has been developed.Mono- and di-N-protected α-amino-β-lactones 3a (L, R1=H, R2=COOCH2Ph (Z)), 3b (D, R1=H, R2=Z), 3c (L, R1=CH2Ph, R2=Z), and 3d (D, R1=CH2Ph, R2=Z) are readily produced by cyclization of the corresponding serine derivatives 2 under modified Mitsunobu conditions without loss of optical purity.Stereochemical integrity was demonstrated by conversion of 3 to 2-methoxy-2-(trifluoromethyl)phenylacetate esters 6 and analysis by HPLC, (19)F NMR, and (1)H NMR.Reaction of 3 with organolithium-derived cuprate reagents (R2CuLi or R2Cu(CN)Li2) at low temperature produces N-protected α-amino acids by attack at the β-methylene group.Yields of di-N-protected amino acids are generally higher (ca. 50-75percent), but some decrease in enantiomeric excess (ee) can occur (0-27percent).In contrast, the mono-N-protected β-lactones 3a and 3b give slightly lower yields (ca. 44-62percent) but negligible decrease in ee (0-1.7percent) with the exception of Ph2Cu(CN)Li2 (67percent loss of ee).However, the use of Cu(I)-catalyzed Grignard (RMgCl) additions gives better yields (44-83percent), complete retention of optical purity ( 99.4percent), and fewer side products.Reductive removal of the protecting groups in a single step (H2/Pd-C or Na/NH3) affords the free α-amino acids in 91-99percent yield.Their stereochemical purity was determined by conversion to the corresponding N-(-)-camphanoyl methyl esters and analysis by gas chromatography and (1)H NMR spectroscopy.