140866-87-1

Basic information

• Product Name: 3-{(2R,3S)-4-Oxo-1-phenoxycarbonylmethyl-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid phenyl ester
• Synonyms: 3-{(2R,3S)-4-Oxo-1-phenoxycarbonylmethyl-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid phenyl ester
• CAS NO: 140866-87-1
• Molecular Weight: 569.614
• Mol File: 140866-87-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-{(2R,3S)-4-Oxo-1-phenoxycarbonylmethyl-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid phenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-{(2R,3S)-4-Oxo-1-phenoxycarbonylmethyl-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid phenyl ester(140866-87-1)
• EPA Substance Registry System: 3-{(2R,3S)-4-Oxo-1-phenoxycarbonylmethyl-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid phenyl ester(140866-87-1)

Safety Data

• Hazardous Substances Data: 140866-87-1(Hazardous Substances Data)

Upstream product

• 140866-86-0 3-{(2R,3S)-1-Carboxymethyl-4-oxo-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid 
• 108-95-2 phenol 
• 135382-83-1 (2S,3R)-3-[(2S,3S)-1-tert-Butoxycarbonylmethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-2-yl]-oxirane-2-carboxylic acid ethyl ester 
• 140925-22-0 (E)-3-[(2R,3S)-1-tert-Butoxycarbonylmethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-2-yl]-acrylic acid ethyl ester 
• 140866-85-9 (2S,3R)-3-[(E)-tert-Butoxycarbonylmethylimino-methyl]-oxirane-2-carboxylic acid ethyl ester 
• 139165-11-0 3-[(2R,3S)-1-tert-Butoxycarbonylmethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-2-yl]-propionic acid ethyl ester 
• 135693-14-0 3-[(2R,3S)-1-Carboxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-2-yl]-propionic acid ethyl ester 

Downstream Products

• 140866-89-3 (6R,7S)-3-Hydroxy-8-oxo-7-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 76497-76-2 (6R*,7S*)-3-chloro-7-amino-8-oxo-1-azabicyclo<4.2.0>oct-2-en-2-carboxylic acid 
• 139165-12-1 (6R,7S)-3-Chloro-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 140866-88-2 3-{(2R,3S)-1-(4-Nitro-benzyloxycarbonylmethyl)-4-oxo-3-[2-(pyrrolidine-1-carbonyl)-benzoylamino]-azetidin-2-yl}-propionic acid phenyl ester 

Relevant articles and documents

Enantioselective synthesis of loracarbef from sodium erythorbate

Sodium erythorbate (7) has been converted to loracarbef (1). Oxidation of sodium erythorbate to D erythronolactone (8) followed by selective monotosylation and treatment with sodium ethoxide provided ethyl (2S,3R) 4 hydroxy 2.3 epoxybutyrate (10). Swern oxidation of this epoxide into the aldehyde (11), imine formation with tert-butylglycinate and an enantioselective Staudinger reaction with phthalimidoacetyl chloride afforded the (3S,4S)-cis-β-lactam (13). Appropriate functional group manipulations followed by a Dieckmann condensation, chlorination, and protecting group removals gave the enantiomerically pure nucleus of loracarbef (24).