187280-57-5

Upstream product

• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 158150-46-0 (3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-3-diphenylmethoxycarbonyl-1-methyl-2-oxopropyl>-2-azetidinone 
• 161683-27-8 (R)-4-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-3-oxo-pentanoic acid benzhydryl ester 
• 159496-98-7 (3S,4R)-3-((1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl)-4-<(1S)-1-(formyl)ethyl>azetidin-2-one 
• 79287-72-2 diphenylmethyl bromoacetate 
• 96613-71-7 4(R)-<1-buten-3(S)-yl>-3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-2-oxoazetidine 
• 91-01-0 1,1-Diphenylmethanol 

Downstream Products

• 147118-02-3 diphenylmethyl (4R,5R,6S)-3-diphenylphosphoryloxy-6-<(1R)-1-hydroxyethyl>-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate 
• 171754-12-4 diphenylmethyl (2R,4R,5R,6S)-6-<(1R)-1-hydroxyethyl>-4-methyl-3,7-dioxo-1-azabicyclo<3.2.0>heptan-2-carboxylate 
• 171754-11-3 diphenylmethyl (2S,4R,5R,6S)-6-<(1R)-1-hydroxyethyl>-4-methyl-3,7-dioxo-1-azabicyclo<3.2.0>heptan-2-carboxylate 
• 158150-46-0 (3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-3-diphenylmethoxycarbonyl-1-methyl-2-oxopropyl>-2-azetidinone 

Relevant academic research and scientific papers

Efficient and practical synthesis of 1β-methylcarbapenems

An efficient and practical method of synthesizing 1β-methylcarbapenem, S-4661, was developed. (4R)-4-[(1S)-1-Methylallyl]-2-azetidinone 2, prepared stereoselectively from commercially available acetoxy-azetidinone 3, was converted to the β-keto ester 6 in four steps. The iodonium ylide 5 was prepared from 6, then cyclized to obtain the bicyclic β-keto ester 4. Finally, 4 was processed to the target product, S-4661, by conventional procedures.

Novel and Efficient Synthesis of 1β-Methylcarbapenems Utilizing Cyclization of Hypervalent Iodonium Ylides

1β-Methylcarbapenems were efficiently synthesized utilizing acid- and rhodium(II)-catalyzed cyclization of iodonium ylide intermediates, which were easily prepared from the corresponding β-keto ester derivatives.