76454-55-2Relevant academic research and scientific papers
Process enabling and the scale-up of 6β-hydroxymethylsulbactam and its esters
Norris, Timothy,Ripin, David H. Brown,Ahlijanian, Paul,Andresen, Brian M.,Barrila, Mark T.,Colon-Cruz, Roberto,Couturier, Michel,Hawkins, Joel M.,Loubkina, Ioulia V.,Rutherford, Jennifer,Stickley, Kurt,Wei, Lulin,Vollinga, Roel,De Pater, Robert,Maas, Peter,De Lange, Ben,Callant, Dominique,Konings, Jeroen,Andrien, Jean,Versleijen, Jos,Hulshof, Jos,Daia, Elena,Johnson, Natalka,Sung, David W. L.
, p. 432 - 439 (2012/12/25)
The optimization of the synthesis of 6β-hydroxymethylsulbactam is described. The primary challenge in this synthesis is the installation of the 6β-hydroxymethyl group with the proper stereochemistry. Engineering challenges associated with the addition of gaseous formaldehyde to a Grignard reagent at low temperature and a number of approaches to achieving the appropriate β-stereochemistry are presented.
Stereoselective Preparation of 6-β-Bromopenicillanic Acid Derivatives
Lukic, Irena
, p. 1 - 4 (2007/10/02)
A new stereoselective method for the preparation of 6-β-bromopenicillanates is described.It comprises the reaction of 6,6-dibromopenicillanates with silver nitrate in 2-propanol.
STEREOSELECTIVE PREPARATION OF 6β-SUBSTITUTED PENICILLANATES. TRI-ORGANOTIN HYDRIDE REDUCTION OF 6-ISOCYANO-, 6-PHENYLSELENENYL-, 6-HALO-, AND 6-ISOTHIOCYANATO-PENICILLANATES
John, D. Ivor,Tyrrell, Nicholas D.,Thomas, Eric J.
, p. 2477 - 2484 (2007/10/02)
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.
