104362-85-8

Upstream product

• 86207-21-8 (3SR,4SR)-4-carboxy-1-(di-p-anisylmethyl)-3-<(SR)-1-hydroxyethyl>-2-azetidinone 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 19293-62-0 p,p'-dimethoxybenzhydrylamine 
• 86207-14-9 [(E)-Bis-(4-methoxy-phenyl)-methylimino]-acetic acid butyl ester 
• 86207-21-8 (3SR,4SR)-4-carboxy-1-(di-p-anisylmethyl)-3-<(RS)-1-hydroxyethyl>-2-azetidinone 
• 91538-19-1 (3SR,4SR)-4-benzyloxycarbonyl-1-(di-p-anisylmethyl)-3-<(SR)-1-hydroxyethyl>-2-azetidinone 
• 91538-19-1 (3SR,4SR)-4-benzyloxycarbonyl-1-(di-p-anisylmethyl)-3-<(RS)-1-hydroxyethyl>-2-azetidinone 
• 67-56-1 methanol 
• 86258-97-1 (3S,4S)-4-carboxy-1-(di-p-anisylmethyl)-3-<(R)-1-hydroxyethyl>-2-azetidinone 
• 86207-16-1 (3RS,4SR)-4-carboxy-1-(di-p-anisylmethyl)-3-ethenyl-2-azetidinone 
• 86207-15-0 (3RS,4RS)-4-n-butoxycarbonyl-1-(di-p-anisylmethyl)-3-ethenyl-2-azetidinone 
• 91538-18-0 3-acetyl-1-(di-p-anisylmethyl)-4-benzyloxycarbonyl-2-azetidinone 

Downstream Products

• 137683-87-5 1-(di-p-anisylmethyl)-(E)-3-ethylidene-4-SR-methoxycarbonyl-2-azetidinone 
• 137664-90-5 1-(di-p-anisylmethyl)-(Z)-3-ethylidene-4-SR-methoxycarbonyl-2-azetidinone 
• 104362-86-9 (3S,4S)-1-(di-p-anisylmethyl)-3-<(R)-1-hydroxyethyl>-4-(1-hydroxy-1-methylethyl)-2-azetidinone 
• 93711-85-4 (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid 
• 143139-22-4 (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-(1-methylethenyl)-2-azetidinone 
• 104362-57-4 (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-(1-hydroxymethylethenyl)-2-azetidinone 
• 104362-56-3 (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-(1-chloromethylethenyl)-2-azetidinone 
• 104362-99-4 (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-<(R)-1-carboxyethyl>-2-azetidinone 
• 112057-69-9 Carbonic acid benzyl ester (R)-1-{(2R,3S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-4-oxo-azetidin-3-yl}-ethyl ester 
• 105557-93-5 Carbonic acid benzyl ester (R)-1-{(2R,3S)-2-[1-methyl-2-(tetrahydro-pyran-2-yloxy)-ethyl]-4-oxo-azetidin-3-yl}-ethyl ester 
• 143139-23-5 (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-(1-tert-butyldimethylsilyloxymethylethenyl)-2-azetidinone 
• 104362-83-6 (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-<1-(2-tetrahydropyranyloxy)methylethenyl>-2-azetidinone 
• 104362-59-6 (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-1-tert-butyldimethylsilyl-4-(1-tert-butyldimethylsilyloxymethylethenyl)-2-azetidinone 
• 104362-92-7 Carbonic acid benzyl ester (R)-1-[(2R,3S)-2-[1-methyl-2-(tetrahydro-pyran-2-yloxy)-ethyl]-4-oxo-1-(tetrahydro-pyran-2-yl)-azetidin-3-yl]-ethyl ester 

Relevant academic research and scientific papers

Beta-lactams and their production

A beta-lactam compound of the formula: STR1 wherein R1 and R2 are, the same or different, each a hydrogen atom or a lower alkyl group, R30 is a hydroen atom or a lower alkyl group having a beta-configuration, R4 is a carboxyl-protecting group, X is a hydrogen atom or a protected hydroxyl group and COZ is a protected thiolcarboxyl group, which is useful as a valuable intermediate in the stereospecific production of 1-alkylcarbapenem compounds.

Synthetic studies of carbapenem and penem antibiotics. III. A synthesis of a key intermediate for 1β-methylcarbapenem

We synthesized useful intermediates 5 and 6 for 1β- and 1α-methylcarbapenems from 4-carboxy-3-[(R)-1-hydroxyethyl]-2-azetidinone 4 as a starting material by using stereoselective hydrogenation and hydroboration, respectively. A practical synthetic route from 4 to the (3S,4S)-4-[(R)-1-carboxyethyl]-3-[(R)-1-hydroxyethyl]-2-azetidinone derivative 1, a useful intermediate for the synthesis of 1β-methylcarbapenem antibiotics, was established.

Synthetic studies of carbapenem and penem antibiotics. I. Facile synthesis of a key intermediate: 4-Acetoxy-3-(1-hydroxyethyl)-2-azetidinone

A highly efficient synthesis of (3R,4R)-4-acetoxy-3-[(R)-1-hydroxyethyl]-2-azetidinone, which is a key intermediate for the synthesis of carbapenem and penem antibiotics, was accomplished. It was found that oxymercuration-reduction of easily obtainable 4-alkyloxycarbonyl-1-(di-p-anisylmethyl)-3-ethenyl-2-azetidinone could be employed as a key stereoselective reaction. The chiral starting material was obtained by optical resolution or asymmetric (2 + 2) cycloaddition. The desired product was afforded in four steps, that is, oxymercuration-reduction, oxidative decarboxylation, protection of the hydroxy group and removal of the N-protecting group.

Beta-lactams and their production via stereospecific hydrogenation

A beta-lactam compound of the formula: STR1 wherein R1 is a hydrogen atom, a lower alkyl group or a 1-hydroxy(lower)alkyl group wherein the hydroxyl group is optionally protected, R2 is a hydrogen atom or a protective group for the n