75666-47-6

Upstream product

• 84208-62-8 (3S,4R)-3-(benzyloxycarbonylamino)-4-(1'-oxo-ethyl)-azetidin-2-one 
• 96851-04-6 ((2S,3S)-2-Acetoxy-3-benzyloxycarbonylamino-4-oxo-azetidin-1-yl)-oxo-acetic acid methyl ester 
• 96947-34-1 6β-benzyloxycarbonylamino-1ξ-oxo-1λ⁴-penicillanic acid methyl ester 
• 139111-02-7 (1'R,3S,4R)-3-(benzyloxycarbonylamino)-4-(1'-hydroxyethyl)-azetidin-2-one 
• 139111-01-6 (1'R,3S,4R)-3-(benzyloxycarbonylamino)-4-(1'-tert-butyldimethylsilyloxy-ethyl)-azetidin-2-one 
• 81651-37-8 methyl (3S,5R,6R)-6-benzyloxycarbonylamino-2,2-dimethylpenam-3-carboxylate 
• 83879-99-6 methyl 2-((3S,4S)-4-acetoxy-3-benzyloxycarbonylaminoazetidin-2-on-1-yl)-3-methylbut-2-enoate 
• 96851-01-3 (2R) methyl 2-((3S,4S)-4-acetoxy-3-benzyloxycarbonylaminoazetidin-2-on-1-yl)-3-methylbut-3-enoate 
• 64-19-7 acetic acid 

Downstream Products

• 142560-72-3 trans-3-benzyloxycarbonylamino-4-methoxycarbonylmethyl-2-azetidinone 
• 87657-61-2 (2R-trans)-<4-oxo-3<<(phenylmethoxy)carbonyl>amino>-2-azetidinyl>(phenylthio)propanedioic acid dimethyl ester 
• 142466-73-7 trans-3-benzyloxycarbonylamino-4-ethoxycarbonylmethyl-2-azetidinone 
• 80582-04-3 (3S-trans)-3-[[(phenylmethoxy)carbonyl]amino]-4-methyl-2-azetidinone 
• 142466-75-9 ((2S,3S)-3-Benzyloxycarbonylamino-4-oxo-azetidin-2-yl)-acetic acid benzyl ester 
• 142466-74-8 trans-3-benzyloxycarbonylamino-4-t-butyloxycarbonylmethyl-2-azetidinone 
• 80082-81-1 benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamate 
• 35592-67-7 (3S,4S)-4-acetoxy-3-phenoxyacetamido-azetidin-2-one 
• 85027-68-5 (2S-trans)-N-<2-(acetyloxy)-4-oxo-3-azetidinyl>benzeneacetamide 
• 205493-74-9 (3S,4S)-3-(1-N-benzyloxycarbonyl-2-indolinecarbonyl)-amino-4-acetoxy-azetidin-2-one 
• 184105-34-8 (3S,4S)-3-(2S-2-benzyloxycarbonylamino-2-phenylmethyl-acetamido)-4-acetoxy-azetidin-2-one 
• 142466-77-1 trans-3-benzyloxycarbonylamino-4-t-butyloxycarbonylmethylcarbamoylmethyl-2-azetidinone 
• 142466-76-0 trans-3-benzyloxycarbonylamino-4-carboxymethyl-2-azetidinone 
• 205493-76-1 Acetic acid (2S,3S)-3-((S)-2-benzyloxycarbonylamino-2-phenyl-acetylamino)-4-oxo-azetidin-2-yl ester 

Relevant academic research and scientific papers

Synthesis and antibacterial activity of C4 substituted monobactams

The synthesis and antibacterial activity of a series of monobactams having substituents at C4 position is described. An efficient route to versatile intermediates 4a-c from 6-aminopenicillanic acid (6-APA) has been developed. Derivatives 10e, 11, 21 showe

β-lactams from ester enolates and silylimines: An enantiospecific synthesis of monocyclic β-lactams

Optically active 3,4-disubstituted azetidin-2-ones have been prepared by annelation of chiral silylimines derived from (S) or (R)-lactaldehyde with the ester enolate of the ethyl 2,2,5,5-tetramethyl-1,2,5-azadisilolidin-1-acetate (STABASE). Oxidation of the hydroxyethyl side chain on the C-4 position of the β-lactam ring, followed by Baeyer-Villiger oxidation led to the optically active (3S, 4S) 3-amino-4-acetoxy-β-lactam. The absolute configuration of this compound was determined by elaboration of this substrate to a key intermediate in the synthesis of the antibiotic 'Aztreonam'. Nucleophilic displacement of the acetoxy group led to optically active 3-amino-4-alkyl(aryl)-azetidin-2-ones.

Reduction process for the preparation of 4-unsubstituted azetidin-2-ones

Novel process for the preparation of azetidin-2-ones of the formula STR1 wherein R1 and R2 independently from each other are hydrogen, or an organic group linked to the ring carbon via a carbon atom, a nitrogen atom or an oxygen atom, characterized in that a corresponding 4-acyloxyazetidin-2-one, which is substituted by a group --O--CO--R3 at the 4-position, wherein R3 is hydrogen or an organic radical stable at the reaction conditions, is reacted with a complex metal hydride comprising reactive hydride ions, such as, lithium borohydride, sodium borohydride, potassium borohydride, zinc borohydride or tetraorganoammonium borohydride.

A NOVEL PREPARATION OF 4-UNSUBSTITUTED β-LACTAMS

The key intermediate (1) for monobacyam synthesis has been prepared from 6-aminopenicillanic acid (6-APA) without using Raney nickel.Desulfurization was accomplished by a two step process, involving a novel reduction reaction.

Clavulanic acid derivatives their preparation and use

This invention provides the compounds of the formula (II): STR1 and salts and esters thereof, wherein R1 is H and R3 is H or an aryl, aralkyl, lower alkyl or substituted lower alkyl group or R1 and R3 are joined