64232-07-1

Upstream product

• 6780-38-7 N-phthaloylglycine chloride 
• 63856-16-6 trimethyl <αR,α'R,α''R>-α,α',α''-tri(4-benzyloxyphenyl)hexahydro-1,3,5-triazine-1,3,5-triacetate 
• 78246-50-1 (R)-(4-Benzyloxy-phenyl)-[(R)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-propionylamino]-acetic acid methyl ester 
• 78246-50-1 (S)-(4-Benzyloxy-phenyl)-[(S)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-propionylamino]-acetic acid methyl ester 
• 29588-89-4 (2S)-2-(1,3-dioxoisoindolin-2-yl)-3-hydroxypropanoic acid 
• 908066-52-4 4-O-benzyl-p-hydroxyphenyl L-glycine methyl ester 
• 78246-50-1 methyl (L)-N^α-phthaloylseryl-(D)-p-benzyloxyphenylglycinate 
• 29588-89-4 N-phthaloyl-L-serine 
• 71336-83-9 methyl D-(p-benzyloxyphenyl)glycinate 
• 88143-74-2 (R)-1-(4-(benzyloxy)phenyl)-2-methoxy-2-oxoethan-1-aminium chloride 

Downstream Products

• 78246-51-2 (S)-(4-Benzyloxy-phenyl)-[(S)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-oxo-azetidin-1-yl]-acetic acid methyl ester 
• 71336-84-0 methyl (3S,αR)-2-(2-oxo-3-phthalimido-1-azetidinyl)-2-(4-hydroxyphenyl)acetate 
• 78246-52-3 (S)-[(S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-oxo-azetidin-1-yl]-(4-hydroxy-phenyl)-acetic acid methyl ester 
• 67509-41-5 3-aminonocardicinic acid hydrochloride 
• 114968-38-6 2-<3-(2-hydroxyimino-2-phenylacetamido)-2-oxo-1-azetidinyl>-2-(4-hydroxyphenyl)acetic acid 

Relevant academic research and scientific papers

The direct chemical conversion of peptides to β-lactams

Appropriately protected seryldipeptides which have a relatively acidic proton (H1 of 1) on the α' C can be efficiently converted to β-lactams by reaction with azodicarboxylates and triphenylphosphine. Application of the same reaction conditions to serylamides which lack an acidic α' proton provided dehydropeptides as the major product. Model reactions and potential intermediates which rationalize these results are described.

Nocardicin A: Stereochemical and Biomimetic Studies of Monocyclic β-Lactam Formation

Using 3H/14C doubly labeled specimens of L- and D-serine bearing tritium label at C-2, biosynthetic studies of norcardicin A (1) produced by whole cells of Nocardia uniformis subsp. tsuyamanensis (ATCC 21806) are reported that indicate (a) that D-serine i

IMPROVED ASYMMETRIC SYNTHESIS OF (-)-3-AMINOCARDICINIC ACID AND FURTHER OBSERVATIONS OF THE MITSUNOBU REACTION FOR β-LACTAM FORMATION IN SERYL PEPTIDES

Protected seryl peptide 2 was treated under a variety of conditions with triphenylphosphine or triethylphosphine and diethyl azodicarboxylate to give mechanistic insight into the β-lactam forming reaction and an improved route to (-)-3-aminocardicinic aci