133789-03-4

Upstream product

• 2100-17-6 4-pentenal 
• 701-99-5 Phenoxyacetyl chloride 
• 299208-74-5 Methanesulfonic acid (S)-1-[(S)-2-oxo-1-(2-phenoxy-acetylamino)-2-sulfoamino-ethyl]-pent-4-enyl ester 
• 35592-67-7 (3S,4S)-4-acetoxy-3-phenoxyacetamido-azetidin-2-one 
• 133789-01-2 N-[(2S,3R)-2-Benzenesulfonyl-2-but-3-enyl-1-(tert-butyl-dimethyl-silanyl)-4-oxo-azetidin-3-yl]-2-phenoxy-acetamide 
• 133789-00-1 N-[(2S,3R)-2-Benzenesulfonyl-1-(tert-butyl-dimethyl-silanyl)-4-oxo-azetidin-3-yl]-2-phenoxy-acetamide 
• 88002-47-5 (3R-trans)-3-phenoxyacetylamino-4-phenylsulfonyl-2-azetidinone 
• 133789-02-3 N-((2S,3R)-2-Benzenesulfonyl-2-but-3-enyl-4-oxo-azetidin-3-yl)-2-phenoxy-acetamide 
• 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 

Downstream Products

• 131533-72-7 3-[(2R,3S)-1-(4-Nitro-benzyloxycarbonylmethyl)-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-2-yl]-propionic acid 
• 299208-76-7 [(2R,3S)-2-But-3-enyl-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-acetic acid 4-nitro-benzyl ester 
• 124831-37-4 cis-4-oxo-3-[(phenoxyacetyl)amino]-2-azetidinepropanoic acid 

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.

Stereoselective Synthesis of Cis-Substituted Azetidinones from Penicillin: a Formal Total Synthesis of Loracarbef

A new method for the synthesis of chiral azetidinones bearing a carbon-carbon bond at the 4-position is described.The preparation involves a stereoselective alkylation-reduction of a silylated 4-phenylsulfonyl azetidinone.The utility of this method was demonstrated by a formal total synthesis of loracarbef.