131533-72-7

Upstream product

• 99333-65-0 1-benzyl-3β-((S)-2-oxo-4-phenyloxazolidin-3-yl)-4β-[2-(2-furyl)ethyl]azetidin-2-one 
• 124831-36-3 N-[(2R,3S)-2-(2-Furan-2-yl-ethyl)-4-oxo-azetidin-3-yl]-2-phenoxy-acetamide 
• 110289-29-7 (3S,4R)-3-amino-4-[2-(furan-2-yl)ethyl]azetidin-2-one 
• 299208-76-7 [(2R,3S)-2-But-3-enyl-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-acetic acid 4-nitro-benzyl ester 
• 299208-74-5 Methanesulfonic acid (S)-1-[(S)-2-oxo-1-(2-phenoxy-acetylamino)-2-sulfoamino-ethyl]-pent-4-enyl ester 
• 299208-73-4 Methanesulfonic acid (S)-1-[(S)-carbamoyl-(2-phenoxy-acetylamino)-methyl]-pent-4-enyl ester 
• 299208-71-2 (2S,3S)-3-Hydroxy-2-(2-phenoxy-acetylamino)-hept-6-enoic acid amide 
• 299208-69-8 (2S,3S)-3-Hydroxy-2-(2-phenoxy-acetylamino)-hept-6-enoic acid 
• 162845-86-5 2S,3S-2-amino-3-hydroxy-6-heptenoic acid 
• 133789-03-4 N-((2R,3S)-2-But-3-enyl-4-oxo-azetidin-3-yl)-2-phenoxy-acetamide 
• 701-99-5 Phenoxyacetyl chloride 
• 131533-61-4 [(2R,3S)-2-(2-Furan-2-yl-ethyl)-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-acetic acid 4-nitro-benzyl ester 

Downstream Products

• 119892-46-5 p-nitrobenzyl 7β-[(phenoxyacetyl)amino]-3-hydroxy-1-carba-1-dethia-3-cephem-4-carboxylate 
• 131533-82-9 [(3S,4R)-2-Oxo-3-(2-phenoxy-acetylamino)-4-(2-phenylsulfanylcarbonyl-ethyl)-azetidin-1-yl]-acetic acid 4-nitro-benzyl ester 

Relevant academic research and scientific papers

Enantioselective syntheses of 1-carbacephalosporins from chemoenzymically derived β-hydroxy-α-amino acids: Applications to the total synthesis of carbacephem antibiotic loracarbef

Serine hydroxymethyltransferase (SHMT) derived from recombinant E. coli was found to be able to catalyze the condensation between glycine and 4-pentenaldehyde, affording enantiopure L-erythro-2-amino-3-hydroxy-6-heptenoic acid (AHHA) in high yield and throughput. Conversion of this chiral intermediate of biosynthetic origin to the oral carbacephalosporin antibiotic loracarbef (Lorabid) via β-lactam forming reactions and subsequent Dieckmann cyclization was achieved. (C) 2000 Elsevier Science Ltd.

Synthesis of carbacephem antibiotics: Synthesis via Dieckmann reaction using phenyl esters to direct the regioselectivity of the cyclization

β-Ketoesters useful for elaboration to carbacephems were synthesized from a variety of enantiomerically pure diesters. Use of phenyl esters to direct the regioselectivity was demonstrated.