74481-22-4

Upstream product

• 1254-56-4 benzyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 
• 50269-19-7 C₂₃H₂₃N₃O₅S 
• 15058-70-5 6-diazopenicillanic acid benzyl ester 
• 645-96-5 Benzeneselenol 
• 1666-13-3 diphenyl diselenide 
• 15058-70-5 benzyl (2S)-6-diazo-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 

Downstream Products

• 62263-79-0 benzyl (2S,5R,6R)-6-<(R)-1-hydroxyethyl>penicillanate 
• 85253-94-7 benzyl 2-<(3S,4R)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-methylsulfonyl-2-oxo-1-azetidinyl>-3-methyl-2-butenoate 
• 83162-14-5 (2S,5R,6R)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 
• 83204-40-4 benzyl (2S,5R,6R)-6-<(R)-1-(t-butyldimethylsilyloxy)ethyl>penicillanate 1,1-dioxide 
• 85253-93-6 (2S,5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 
• 83212-60-6 benzyl (2S,5R,6S)-6-<(R)-1-hydroxyethyl>-6-(phenylseleno)penicillanate 
• 83204-40-4 (2S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 
• 83204-40-4 (2S,6R)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 
• 62263-73-4 (2S,6R)-6-((R)-1-Hydroxy-ethyl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 
• 83162-13-4 (2S,6S)-6-((R)-1-Hydroxy-ethyl)-3,3-dimethyl-7-oxo-6-phenylselanyl-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 
• 83162-13-4 (2S,6R)-6-((S)-1-Hydroxy-ethyl)-3,3-dimethyl-7-oxo-6-phenylselanyl-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 
• 74481-23-5 benzyl (2S,5R,6R)-6-(phenylseleno)penicillanate 
• 74481-12-2 (2S,6R)-3,3-Dimethyl-7-oxo-6-phenylselanyl-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Preparation of 6α-Monosubstituted and 6,6-Disubstituted Penicillanates from 6-Diazopenicillanates: Reactions of 6-Diazopenicillanates with Alcohols, Thiols, Phenylseleninyl Compounds, and Allylic Sulphides, and their Analogues

Reactions of 6-diazapenicillanates (1) and (2) with a range of compounds, in some cases catalysed by BF3-Et2O or Cu(acac)2, have been investigated, and found to be useful for the synthesis of 6α-monosubstituted and 6,6-disubstituted penicillanates.Thus th

FROM PENICILLIN TO PENEM AND CARBAPENEM. II. SYNTHESIS OF 3,4-DISUBSTITUTED AZETIDINONE DERIVATIVES FROM 6,6-BIS(PHENYLSELENYL)PENICILLANATE

6,6-Bis(phenylselenyl)penicillanate 2a was converted into 6-1'-(R)-hydroxyethyl substituted penicillanate 5 in high yield.Compound 5 was deselenylated to 10.Oxidation, and then the basic epimerization of cis sulfone 11 gave trans sulfone derivative 12.The trans sulfone 12 was degraded to the monocyclic β-lactams 14, 15 which are important precursors for the carbapenem synthesis.

Preparation and reduction of 6-phenylselenylpenicillanates. A stereoselective synthesis of 6β-substituted penicillanates

The preparation and tri-n-butyltin hydride reduction of benzyl 6-chloro-6-phenyl-selenyl- and benzyl 6,6-bis(phenylselenyl)penicillanates, and related compounds, is discussed.