104362-52-9

Upstream product

• 104380-26-9 (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-1-(di-p-anisylmethyl)-4-(1-hydroxyl-1-methylethyl)-2-azetidinone 
• 86258-97-1 (3S,4S)-4-carboxy-1-(di-p-anisylmethyl)-3-<(R)-1-hydroxyethyl>-2-azetidinone 
• 104362-85-8 (3S,4S)-1-(di-p-anisylmethyl)-3-<(R)-1-hydroxyethyl>-4-methoxycarbonyl-2-azetidinone 
• 104362-86-9 (3S,4S)-1-(di-p-anisylmethyl)-3-<(R)-1-hydroxyethyl>-4-(1-hydroxy-1-methylethyl)-2-azetidinone 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 105318-33-0 (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-(1-chloromethylethenyl)-1-(di-p-anisylmethyl)-2-azetidinone 
• 104363-00-0 (3S,4R)-3-<(R)-1-benzyloxycarbonyloxyethyl>-1-(di-p-anisylmethyl)-4-<(R)-1-hydroxymethylethyl>-2-azetidinone 
• 104420-11-3 (3S,4R)-3-<(R)-1-benzyloxycarbonyloxyethyl>-1-(di-p-anisylmethyl)-4-<(S)-1-hydroxymethylethyl>-2-azetidinone 
• 104362-98-3 (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-<(R)-1-hydroxymethylethyl>-2-azetidinone 
• 143170-17-6 (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-<(S)-1-hydroxymethylethyl>-2-azetidinone 
• 104362-94-9 Carbonic acid benzyl ester (R)-1-{(2R,3S)-1-[bis-(4-methoxy-phenyl)-methyl]-2-[1-methyl-2-(methyl-diphenyl-silanyloxy)-ethyl]-4-oxo-azetidin-3-yl}-ethyl ester 
• 104380-28-1 (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-1-(di-p-anisylmethyl)-4-(1-diphenylmethylsilyloxymethylethenyl)-2-azetidinone 
• 104362-58-5 (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-(1-tert-butyldimethylsilyloxymethylethenyl)-1-(di-p-anisylmethyl)-2-azetidinone 
• 104362-95-0 Carbonic acid benzyl ester (R)-1-{(2R,3S)-1-[bis-(4-methoxy-phenyl)-methyl]-2-[1-methyl-2-(tetrahydro-pyran-2-yloxy)-ethyl]-4-oxo-azetidin-3-yl}-ethyl ester 
• 104362-81-4 (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-1-(di-p-anisylmethyl)-4-<1-(2-tetrahydropyranyloxy)methylethenyl>-2-azetidinone 
• 104362-55-2 (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-1-(di-p-anisylmethyl)-4-(1-hydroxymethylethenyl)-2-azetidinone 
• 104362-82-5 (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-1-(2-tetrahydropyranyl)-4-<1-(2-tetrahydropyranyloxy)methylethenyl>-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 
• 104362-59-6 (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-1-tert-butyldimethylsilyl-4-(1-tert-butyldimethylsilyloxymethylethenyl)-2-azetidinone 

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.