101765-69-9

Upstream product

• 115026-51-2 (S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(R)-2-(4,4-dimethyl-2-thioxo-oxazolidin-3-yl)-1-methyl-2-oxo-ethyl]-azetidin-2-one 
• 108-98-5 thiophenol 
• 1138247-25-2 trimethyl-(1-phenylsulfanyl-propenyloxy)-silane 
• 86978-81-6 Acetic acid (2R,3R)-3-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-1-trimethylsilanyl-azetidin-2-yl ester 
• 18245-72-2 S-phenylthiopropionate 
• 80951-41-3 4-acetoxy-3-(1-t-butyl-dimethylsilyloxy)ethyl-2-azetidinone 
• 101765-66-6 Trimethyl-((E)-1-phenylsulfanyl-propenyloxy)-silane 
• 76899-07-5 (3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one 
• 119891-99-5 tert-Butyl-dimethyl-((E)-1-phenylsulfanyl-propenyloxy)-silane 
• 156630-83-0 5-[(2S,3S)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-oxoazetidin-2-yl]-2,2,5-trimethyl[1,3]dioxane-4,6-dione 

Downstream Products

• 101135-08-4 (4S,5S,6S)-6-(1-Hydroxy-ethyl)-4-methyl-3-((S)-1-{1-[(E)-4-nitro-benzyloxycarbonylimino]-ethyl}-pyrrolidin-3-ylsulfanyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 90776-59-3 (4S,5R,6S)-3-(Diphenoxy-phosphoryloxy)-6-(1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 101135-09-5 1-α-methyl RS-533 
• 83973-55-1 (2R,4S,5R,6S)-6-(1-Hydroxy-ethyl)-4-methyl-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester 
• 101151-51-3 (4R,5S,6S)-6-(1-Hydroxy-ethyl)-4-methyl-3-[(S)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 90776-59-3 (4R,5R,6S)-3-(Diphenoxy-phosphoryloxy)-6-(1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 101135-09-5 1-β-methyl RS-533 
• 83973-55-1 (2R,4R,5R,6S)-6-(1-Hydroxy-ethyl)-4-methyl-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester 
• 90776-58-2 (R)-2-{(2S,3S)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-propionic acid 
• 90776-58-2 (R)-2-{(2S,3S)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-propionic acid 
• 90776-58-2 (S)-2-{(2S,3S)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-propionic acid 

Relevant academic research and scientific papers

1β-Methylcarbapenem intermediates via the thiolysis of a Meldrum's precursor

5-{3-[1-(tert-Butyldimethylsilyloxy)ethyl]-4-oxo-azetidin-2-yl}-2,2,5- trimethyl-[1,3]dioxane-4,6-dione (3) has been submitted to nucleophilic attack with various nucleophiles. Meldrum's moiety transesterification, C4-substitution, β-lactam ring opening and Meldrum's moiety decarboxylation were observed. Reaction of 3 with ethanethiol and dimethylaminopyridine in ethanol quantitatively furnished ethyl 2-{3-[1-(tert-butyldimethylsilyloxy)ethyl]-4-oxo-azetidin-2-yl}- thiopropionate as the 1:1 mixture of β (7a) and α (8a) diastereoisomers.

SYNTHESIS OF 1-β-METHYLCARBAPENEM KEY INTERMEDIATES INVOLVING THE LABILE ACYL AUXILIARY 4,4-DIMETHYL-1,3-OXAZOLIDINE-2-THIONE

A convenient synthesis of 1-β-methylcarbapenem key intermediates based on the facile displacement of the 4,4-dimethyl-1,3-oxazolidine-2-thione auxiliary of 5 is described.

STEREOSELECTIVE SYNTHESIS OF 1-β-METHYLCARBAPENEM

Stereoselective syntheses of the 1-β-methylcarbapenem intermediates 9B (R=SPh or OCH3) have been accomplished by an aldol-type stereocontrolled reaction and stereoselective catalytic hydrogenation of an olefinic ester.

Synthetic study of 1-substituted carbapenem antibiotics

Total synthesis of 1-substituted carbapenems is described. The key step is the reaction of acetoxyazetidinone with ketene silyl acetal.