78385-35-0

Upstream product

• 78385-36-1 benzyloxycarbonylmethyltriphenylphosphonium bromide 
• 603-35-0 triphenylphosphine 
• 15097-38-8 (carbobenzyloxymethylene)triphenylphosphorane 
• 5437-45-6 Benzyl bromoacetate 

Downstream Products

• 78385-37-2 benzyl 2-bromocyclopropylideneacetate 
• 5437-45-6 Benzyl bromoacetate 
• 83089-69-4 benzyl 2-bromo-4-methylpenta-2,3-dienoate 
• 83089-70-7 benzyl 2-bromo-4-phenylbuta-2,3-dienoate 
• 78385-38-3 1-<(2R,3R)-4-oxo-3-phenoxyacetamidoazetidin-2-ylthio>-1-(1-benzyloxycarbonyl-1-bromomethyl)cyclopropane 
• 78385-43-0 (3S,5R,6R)-benzyl 6-D-α-aminophenylacetamidocyclopropanespiro-2-bisnorpenicillanate 
• 83089-75-2 (3S,5R,6R)-benzyl 2-benzylidene-6-phenoxyacetamidopenam-3-carboxylate 
• 83089-74-1 (Z)-2-Bromo-3-[(2R,3R)-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-2-ylsulfanyl]-4-phenyl-but-3-enoic acid benzyl ester 
• 83089-71-8 (3S,5R,6R)-benzyl 2-(2-benzyloxyethylidene)-6-phenoxyacetamidopenam-3-carboxylate 
• 83089-84-3 {1-[(2R,3R)-3-(2-Benzyloxycarbonylamino-2-phenyl-acetylamino)-4-oxo-azetidin-2-ylsulfanyl]-cyclopropyl}-bromo-acetic acid benzyl ester 
• 83089-85-4 (3R,5R,6R)-benzyl 6-DL-α-benzyloxycarbonylaminophenylacetamido-cyclopropanespiro-2-bisnorpenicillanate 
• 78385-34-9 (3S,5R,6R)-benzyl 6-aminocyclopropanespiro-2-bisnorpenicillanate 
• 83089-73-0 (3R,5R,6R)-benzyl 6-phenoxyacetamido-2-isopropylidenepenam-3-carboxylate 
• 83089-72-9 (3S,5R,6R)-benzyl 6-phenoxyacetamido-2-isopropylidenepenam-3-carboxylate 

Relevant academic research and scientific papers

Synthetic, mechanistic, and biological interrogation of Ginkgo biloba chemical space en route to (-)-bilobalide

Here we interrogate the structurally dense (1.64 mcbits/?3) GABAA receptor antagonist bilobalide, intermediates en route to its synthesis, and related mechanistic questions. 13C isotope labeling identifies an unexpected bromine migration en route to an α-selective, catalytic asymmetric Reformatsky reaction, ruling out an asymmetric allylation pathway. Experiment and computation converge on the driving forces behind two surprising observations. First, an oxetane acetal persists in concentrated mineral acid (1.5 M DCl in THF-d8/D2O); its longevity is correlated to destabilizing steric clash between substituents upon ring-opening. Second, a regioselective oxidation of des-hydroxybilobalide is found to rely on lactone acidification through lonepair delocalization, which leads to extremely rapid intermolecular enolate equilibration. We also establish equivalent effects of (-)-bilobalide and the nonconvulsive sesquiterpene (-)-jiadifenolide on action potential-independent inhibitory currents at GABAergic synapses, using (+)-bilobalide as a negative control. The high information density of bilobalide distinguishes it from other scaffolds and may characterize natural product (NP) space more generally. Therefore, we also include a Python script to quickly (ca. 132 000 molecules/min) calculate information content (B?ttcher scores), which may prove helpful to identify important features of NP space.

The Chemistry of 4-Mercaptoazetidin-2-ones. Part 3. Synthesis of 6-Phenoxyacetamido-2-alkylidenepenam-3-carboxylic Acids

A general method for the preparation of α-bromoallenic esters (2) involving the reaction of an acid chloride with a carboxybromomethylenetriphenylphosphorane has been developed.Reaction of these esters with the 4-mercaptoazetidin-2-one (1) gave rise to the 2-alkylidenepenam esters (3).The title compounds, obtained by hydrogenolysis of the corresponding benzyl esters, showed only moderate antibacterial properties.