62263-72-3

Upstream product

• 62263-89-2 Benzyl 6α-bromopenicillanate 
• 124831-33-0 (2R,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 35564-99-9 benzyl 6,6-dibromopenicillanate 
• 100-39-0 benzyl bromide 
• 24158-88-1 6,6-dibromopenicillanic acid 
• 124831-32-9 (3S,4R)-4-<<4-(Benzyloxy)-2-methyl-4-nitro-3(Z)-buten-2-yl>thio>-1-(tert-butyldimethylsilyl)-3-(trimethylsilyl)-2-azetidinone 
• 128971-81-3 (3S,4R)-4-<<4-(Benzyloxy)-3-hydroxy-2-methyl-4-nitro-2-butyl>thio>-1-(tert-butyldimethylsilyl)-3-(trimethylsilyl)-2-azetidinone 
• 128971-80-2 (3S,4R)-1-(tert-Butyldimethylsilyl)-4-<(2-methyl-3-buten-2-yl)thio>-3-(trimethylsilyl)-2-azetidinone 
• 128971-79-9 (3S,4R)-4-<(2-Methyl-3-buten-2-yl)thio>-3-(trimethylsilyl)-2-azetidinone 
• 124831-32-9 (3S,4R)-4-((Z)-3-Benzyloxy-1,1-dimethyl-3-nitro-allylsulfanyl)-1-(tert-butyl-dimethyl-silanyl)-3-trimethylsilanyl-azetidin-2-one 
• 124831-31-8 (3S,4R)-1-(tert-Butyldimethylsilyl)-4-<(2-methyl-3-oxo-2-propyl)thio>-3-(trimethylsilyl)-2-azetidinone 
• 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 
• 551-16-6 6-Aminopenicillanic Acid 
• 24138-28-1 6-bromopenicillanic acid 

Downstream Products

• 68373-14-8 sulbactum 
• 303730-72-5 benzyl (2S)-2-[(4S)-4-chloro-2-oxazetidin-1-yl]-2-(1-chlorothio-1-methylethyl)-acetate 
• 76946-53-7 (2S,4R,5R)-3,3-Dimethyl-4,7-dioxo-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 
• 69388-78-9 (2S,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate 4,4-Dioxide 
• 129573-94-0 3-Methyl-2-((R)-2-oxo-4-phenylacetylsulfanyl-azetidin-1-yl)-but-2-enoic acid benzyl ester 
• 112672-62-5 (2S,5R)-7-[1-Methoxycarbonyl-meth-(Z)-ylidene]-3,3-dimethyl-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 
• 112672-63-6 (2S,5R)-7-[1-Methoxycarbonyl-meth-(E)-ylidene]-3,3-dimethyl-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Syntheses of (6S)-cephalosporins from 6-aminopenicillanic acid

Two practical routes to (6S,7S)-cephalosporins from 6-aminopenicillanic acid (6-APA) are described. In the first, 6-APA was converted to (2S,4S,5S,6S)-penicillin sulfoxide 49, which underwent Morin ring expansion to a protected (6S,7S)-cephem 50. In the s

STEREOCONTROLLED TOTAL SYNTHESIS OF THE PENICILLINATE ESTER (2S,5R)-BENZYL 3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLOHEPTANE-2-CARBOXYLATE

(3R)-4-Acetoxy-3-trimethylsilyl-2-azetidinone, was converted into optically pure benzyl penicillinate in seven step (22percent) using (benzyloxy)nitromethane as a reagent for ring annulation.

EFFICIENT PREPARATION OF PENICILLANATE ESTER: A REDUCTIVE DEBROMINATION OF BROMOPENICILLANATE ESTER AND BROMOPENICILLANATE-S,S-DIOXIDE ESTER WITH TRI-N-BUTYLPHOSPHINE

Benzyl bromopenicillanate (5) and benzyl bromopenicillanate-S,S-dioxide (6) were subject to a reductive debromination in an effect of tri-n-butylphosphine furnishing benzyl penicillanate (7) and benzyl penicillanate-S,S-dioxide (8) in 50percent and 81percent yield respectively.

STEREOSELECTIVE PREPARATION OF 6β-SUBSTITUTED PENICILLANATES. TRI-ORGANOTIN HYDRIDE REDUCTION OF 6-ISOCYANO-, 6-PHENYLSELENENYL-, 6-HALO-, AND 6-ISOTHIOCYANATO-PENICILLANATES

6β-Benzyl-, 6β-(2-hydroxyprop-2-yl)-, 6β-methoxycarbonylmethyl-, 6β-methoxycarbonylethyl-, 6β-(t-butoxycarbonylmethyl)-, and 6β-methylthiopenicillanates 10-15 have been prepared stereoselectively by tri-n-butyltin hydride reduction of the corresponding 6β-isocyanopenicillanates 4-9.A minor side-product (15percent) isolated from the reduction of benzyl 6α-(2-hydroxyprop-2-yl)-6β-isocyanopenicillanate 5 was identified as (1R,5R)-6--1-(2-hydroxyprop-2-yl)-2,6-diaza-4-thiabicyclohept-2-en-7-one 18, and small quantities of analogous thiazolines 19 and 20 were detected in the crude mixtures from the reductions of the 6α-benzyl- and 6α-methoxycarbonylmethyl-6β-isocyanopenicillanates 4 and 6.Benzyl and methyl penicillanates 30 and 31 were obtained by tri-n-butyltin hydride reduction of the 6α-brompenicillanates 28 and 29, and reduction of benzyl 6,6-dibromopenicillanate 35 gave a mixture of products in wich the 6β-bromopenicillanate 37 predominated. 6β-Chloro-, 6β-phenylselenenyl-, and 6β-allylpenicillanates 48, 49 and 52 were obtained by tri-n-butyltin hydride reduction of the corresponding 6-phenyl- selenenylpenicillanates 43, 45, 50 and 51. In contrast, tri-organotin hydride reduction of methyl 6β-isothiocyanatopenicillanate 53 was accompanied by sulphur-C(2) bond cleavage to give rearranged thiazoline-azetidinones 54 and 55.