69388-78-9

Upstream product

• 76454-56-3 benzyl bromopenicillanate-S,S-dioxide 
• 62263-72-3 (2S,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 35564-99-9 benzyl 6,6-dibromopenicillanate 
• 76454-54-1 benzyl 6,6-dibromo-1,1-dioxopenicillanate 
• 124831-33-0 (2R,5R)-Benzyl 3,3-Dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate 
• 124831-31-8 (3S,4R)-1-(tert-Butyldimethylsilyl)-4-<(2-methyl-3-oxo-2-propyl)thio>-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 
• 551-16-6 6-Aminopenicillanic Acid 
• 62263-89-2 Benzyl 6α-bromopenicillanate 
• 24138-28-1 6-bromopenicillanic acid 
• 69388-84-7 sodium sulbactam 
• 100-39-0 benzyl bromide 
• 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 

Downstream Products

• 90473-64-6 (2R,4S)-2-Carboxymethyl-5,5-dimethyl-1,1-dioxo-3-(2,2,2-trifluoro-acetyl)-1λ⁶-thiazolidine-4-carboxylic acid benzyl ester 
• 97129-34-5 Sodium; (R)-1-(1-benzyloxycarbonyl-2-methyl-propenyl)-4-oxo-azetidine-2-sulfinate 
• 97129-35-6 benzyl 2-<(2R)-2-acetonylsulphonyl-4-oxo-azetidin-1-yl>-3-methylbut-2-enoate 
• 97129-36-7 benzyl 2-<(2R)-2-acetonylsulphonyl-4-oxoazetidin-1-yl>glyoxylate 
• 97129-37-8 (6R)-4-benzyloxycarbonyl-3-methylceph-3-em 1,1-dioxide 
• 97129-33-4 (2R)-1-(1-benzyloxycarbonyl-2-methylprop-1-enyl)-4-oxoazetidine-2-sulphinic acid 
• 68373-14-8 sulbactum 

Relevant academic research and scientific papers

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.

SOME OBSERVATIONS REGARDING β-LACTAM-CLEAVAGE REACTIONS OF PENICILLANATE 1,1-DIOXIDES AND RELATED COMPOUNDS

1,5-Bond ruptures may follow, but do not accompany, 4,7-bond cleavages of penicillanate 1,1-dioxides.

Total Synthesis of Analogues of the &β-Lactam Antibiotics. Part 2. Isopenam-3-carboxylates and their 2,2-Dioxides

t-Butyl hydroxy-(2-iodomethyl-4-oxoazetidin-1-yl)acetate (10a), as a 1:1 mixture of diastereoisomers, was transformed, by sequential reactions involving thionyl chloride - 2,6-lutidine and hydrogen sulphide - triethylamine, into a 1:1.7 mixture of t-butyl

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.