15058-70-5

Upstream product

• 19912-14-2 (2S,5R,6R)-6-amino-2-(benzyloxycarbonyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane p-toluenesulfonic acid 
• 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 
• 3956-31-8 benzyl (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 

Downstream Products

• 62263-90-5 6α-iodo-penicillanic acid benzyl ester 
• 62263-89-2 Benzyl 6α-bromopenicillanate 
• 35564-99-9 benzyl 6,6-dibromopenicillanate 
• 71972-82-2 (6'R)-5-carbamoyl-3',3'-dimethyl-7'-oxo-2,4-dihydro-(5'tH,6'rN)-spiro[pyrazole-3,6'-(4-thia-1-aza-bicyclo[3.2.0]heptane)]-2't-carboxylic acid benzyl ester 
• 74481-12-2 benzyl (2S,5R,6S)-6-(phenylseleno)penicillanate 
• 74481-08-6 benzyl 6α-allyl-6β-phenylselenopenicillanate 
• 74481-09-7 benzyl 6β-allyl-6α-phenylselenopenicillanate 
• 74481-22-4 benzyl (2S,5R)-6,6-bis(phenylseleno)penicillanate 
• 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 

Relevant academic research and scientific papers

Chiral spiro-β-lactams from 6-diazopenicillanates

Chiral spiro-β-lactam derivatives have been prepared via stereoselective 1,3-dipolar cycloaddition of 6-diazopenicillanates. Using dipolarophiles such as acrylonitrile, acrylates or methyl vinyl ketone spiro-2-pyrazoline-β-lactams were obtained, whereas t

Synthesis Of 6β-Methoxy-6α-Hydroxymethylpenenms

6α-Hydroxymethyl-6β-methoxy-2-phenoxymethylpenem was synthesized from benzyl 6β-bromo-6α-methoxypenicillanate via radical addition at 6α-position of methyl tributyltinacrylate and tributyltinstyrene inter alia.The reaction sequence to penem proceeds via secopenicillanates according to established procedures.The good yield of the radical reaction and its stereoselectivity provide a useful entry to the 6α-substituted 6β-methoxypenems and in particular to the 6α-hydroxymethyl-6β-methoxypenems.

Stereospecific synthesis of thienamycin from penicillin

A stereospecific conversion of penicillin to thienamycin, using diisopropylamine borane and magnesium trifluoroacetate to prepare the hydroxyethyl side chain and acetoacetate dianion equivalent disilylethyl to prepare the β-ketoester side chain.

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

6-Substituted methyl penicillins, derivatives and analogues thereof

Disclosed are antibiotic 6-(substituted methyl) penicillins, derivatives and nuclear analogues thereof; wherein the methyl substituent is, inter alia, hydroxyl, ketonic oxygen, imino nitrogen, amino or thio. Also disclosed are processes for the preparatio

Derivatives of 6-aminopenicillanic acid

Novel 6-methoxy and 6-thioalkyl-6-acylamidopenicillanic acids and their non-toxic pharmaceutically-acceptable salts, esters and amides which are useful as antibiotics. The products are prepared by treating an ester of 6-substituted-6-aminopenicillanic acid with an acylating agent followed by removal of the ester group. Also disclosed are novel intermediates.

6α, β-Substituted penicillin derivatives

Novel 6-methoxy and 6-thioalkyl-6-acylamido-penicillanic acids and their non-toxic pharmaceutically-acceptable salts, esters and amides which are useful as antibiotics. The products are prepared by treating an ester of 6-substituted-6-aminopenicillanic acid with an acylating agent followed by removal of the ester group. Also disclosed are novel intermediates.