397887-06-8

Upstream product

• 140-29-4 phenylacetonitrile 
• 397886-88-3 5-(2-bromo-propionyl)-4-oxo-3-phenyl-1-oxa-5-aza-spiro[5.5]undec-2-ene-2-carboxylic acid methyl ester 
• 203938-96-9 4-Oxo-3-phenyl-1-oxa-5-aza-spiro[5.5]undec-2-ene-2-carboxylic acid methyl ester 
• 108-94-1 cyclohexanone 
• 619-73-8 4-nitrobenzyl chloride 
• 16869-24-2 4-nitrobenzyl bromoacetate 
• 397886-97-4 5-((R)-2-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-propionyl)-4-oxo-3-phenyl-1-oxa-5-aza-spiro[5.5]undec-2-ene-2-carboxylic acid methyl ester 

Downstream Products

• 105318-43-2 p-nitrobenzyl (4R,5R,6S)-6-<(1R)-1-tert-butyldimethylsilyloxyethyl>-3-diphenylphosphoryloxy-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate 

Relevant academic research and scientific papers

2,3-Dihydro-4H-1,3-oxazin-4-ones, novel auxiliaries for the stereoselective synthesis of 1β-methylcarbapenems

Dihydrooxazinones 9, prepared from benzylcyanide in two steps serve as efficient auxiliaries for the stereoselective synthesis of β-methylcarbapenem intermediate 2. Reformatsky-type reactions of 4-acetoxyazetidinone with α-bromopropionyl dihydrooxazinone 10 provided β-methylazetidinones 4 in high diastereoselectivities. The auxiliaries 9 were also easily removed in the Dieckmann cyclization leading to β-methylcarbapenem skeletons. Practical synthesis of β-methylenolphosphates 2 from 4-acetoxyazetidinone 3 was achieved in three steps (61-77% overall yield).