74720-06-2

Basic information

• Product Name: Butanoic acid, 3-(benzoylamino)-, (3S)-
• CAS NO: 74720-06-2
• Molecular Formula: C11H13NO3
• Molecular Weight: 207.229
• Mol File: 74720-06-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Butanoic acid, 3-(benzoylamino)-, (3S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Butanoic acid, 3-(benzoylamino)-, (3S)-(74720-06-2)
• EPA Substance Registry System: Butanoic acid, 3-(benzoylamino)-, (3S)-(74720-06-2)

Safety Data

• Hazardous Substances Data: 74720-06-2(Hazardous Substances Data)

Upstream product

• 3775-72-2 L-3-aminobutyric acid 
• 98-88-4 benzoyl chloride 

Downstream Products

• 74720-10-8 N-(1-Methyl-3-oxo-propyl)-benzamide 
• 381718-65-6 4(S)-(benzoylamino)-1,2-(R and S)-pentanediol 
• 381718-59-8 (S)-3-(benzoylamino)-4-pentene 
• 74720-10-8 (S)-3-(benzoylamino)butyraldehyde 
• 65-85-0 benzoic acid 
• 74720-08-4 (+)-4,5-dihydro-4-methyl-2-phenyl-1,3-oxazin-6-one 
• 113034-32-5 methyl ester of (S)-3-(benzoylamino)butanoic acid 

Relevant articles and documents

Stereospecific synthesis of oligonucleotides containing crotonaldehyde adducts of deoxyguanosine

Crotonaldehyde reacts with DNA to form two diastereomeric 1,N2 cyclic adducts of deoxyguanosine. A synthesis of the two diastereomeric deoxynucleosides has been achieved by reaction of mixed diastereomers of 4-amino-1,2-pentanediol with 2-fluoro-O6-(trimethylsilylethyl)-deoxyinosine. The resulting N2-(1-methyl-3,4-dihydroxybutyl)-deoxyguanosine was treated with NaIO4, cleaving the vicinal diol to the aldehyde. Spontaneous cyclization gave the two diastereomers of the crotonaldehyde-adducted nucleoside that were readily separated by HPLC. The absolute configurations were assigned by an enantiospecific synthesis of one diastereomer from (S)-3-aminobutanoic acid. The synthetic strategy has been extended to preparation of a site-specifically adducted oligonucleotide by reaction of the mixed diastereomers of 4-amino-1,2-pentanediol with an 8-mer oligonucleotide containing 2-fluoro-O6-(trimethylsilylethyl)-deoxyinosine. The diastereomeric oligonucleotides were separated by HPLC and absolute configurations of the adducts were established by enzymatic digestion to the adducted nucleosides.

194. Diastereoselecktive Alkylation of 3-Aminobutanoic Acid in the 2-Position

The enantiomerically pure 3-aminobutanoic acids (R)- and (S)-6 are readily available by preparative HPLC separation of the two diastereoisomers 5 obtained from addition of (S)-phenethylamine to methyl crotonate and subsequent hydrogenolysis (Scheme 2). (S)-methyl 3-(benzoylamino)butanoate ((S)-3) is also available by enzymatic kinetic resolution with pig-liver esterase.The N-benzoyl- and N-benzyloxycarbonyl derivatives rac-3, 8,and 9 of 3-aminobutanoates are doubly deprotonated with LDA and alkylated or aminated in high selectivity (17 examples, relative topicity like; see Tables 1 and 2).The configuration of three of the products is assigned (Schemes 4-6), and in four cases, the free α-substituted β-amino acid is prepared by acidic hydrolysis (see Table 3).It is shown that the doubly lithiated β-amino-acid derivative is solubilized, and its reactivity may be strongly influenced by the presence of 3 equiv. of LiCl.

Selective Hydrogenation of 4,5-Dihydro-1,3-oxazin-6-ones to Carbaldehyde Derivatives; Chemical Differentiation between Acylazetidin-2-ones and the Corresponding Isomeric Oxazin-6-ones

Catalytic hydrogenation of optically active and non-active dihydro-oxazin-6-ones unexpectedly led to preferential reduction of the carbonyl group with ring-opening yielding carbaldehyde derivatives.This reaction resolved a structural problem by leading to