5817-49-2

Upstream product

• 69-96-5 dl-threo-phenylserine 
• 501-53-1 benzyl chloroformate 
• 78498-83-6 (3RS)-7-chloro-1,3-dihydro-3-[(1SR)-hydroxy(phenyl)methyl]-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one 
• 69-96-5 (2RS,3RS)-2-amino-3-hydroxy-3-phenyl-propionic acid 

Downstream Products

• 103642-46-2 (2RS,3SR)-2-benzyloxycarbonylamino-3-hydroxy-3-phenyl-propionic acid benzyloxyamide 
• 93847-72-4 ((1S,2R)-2-Hydroxy-2-phenyl-1-p-tolylcarbamoyl-ethyl)-carbamic acid benzyl ester 
• 93847-79-1 ((3R,4R)-2-Oxo-4-phenyl-1-p-tolyl-azetidin-3-yl)-carbamic acid benzyl ester 
• 93847-83-7 cis-1-carbobenzyloxy-2-phenyl-3-(N-p-tolyl)amidoaziridine 
• 74805-55-3 (Z)-1-anilino-4-benzylideneimidazolidine-2,5-dione 
• 3775-01-7 5-benzylidenehydantoin 
• 74805-47-3 (Z)-1,1-diphenyl-(2-benzyloxycarbonylamino)cinnamyl alcohol 
• 74805-61-1 2-benzyloxy-8-phenyl-1,10-dioxa-3,5,6-triazadispiro<4.4.0.2>dodeca-2,5-diene 
• 74805-45-1 (Z)-N-benzyloxycarbonyldehydrophenylalanylglycine ethyl ester 
• 74805-53-1 N-benzyloxycarbonyl-(Z)-dehydrophenylalanine phenylhydrazide 
• 74805-46-2 N-benzyloxycarbonyl-(Z)-dehydrophenylalanine thiobenzyl ester 
• 74805-58-6 benzyloxycarbonyl-(Z)-dehydrophenylalanine anilide 
• 74805-43-9 (Z)-N-benzyloxycarbonyldehydrophenylalanine azide 
• 74805-44-0 1-(5-benzyloxytetrazol-1-yl)cinnamic acid 

Relevant academic research and scientific papers

syn/anti Diastereoselectivity in the aldol reaction of aldehydes with the C(3) carbanion of 1,3-dihydro-2H-1,4-benzodiazepin-2-one

The aldol reaction of the C(3) carbanion of 7-chloro-1,3-dihydro-1- methyl-5-phenyl-2H-1,4-benzodiazepin-2-one (2) with a series of aromatic and aliphatic aldehydes at -78°afforded threo/erythro diastereoisomers 3-16 of 7-chloro-1,3-dihydro-3-(hydroxymethyl)-1-methyl-5-phenyl-2H-1,4- benzodiazepinones, substituted at the C(3) side chain, in a ratio from 55:45 to 94:6 (Scheme 1). Lewis acids exhibited limited effect on the syn/anti diastereoselectivity of this reaction, and kinetic control of the reaction was confirmed. 1H-NMR Data suggested the assignment of the threo relative configuration to the first-eluted diastereoisomers 3, 5 7, and 9 on reversed- phase HPLC, and the erythro configuration to the second-eluted counterparts 4, 6, 8, and 10, respectively. The structures and relative configurations threo and erythro of the diastereoisomers 5 and 6, respectively, were established by single-crystal X-ray analysis, confirming the assignment based on the 1H-NMR data. A tentative mechanistic explanation of the diastereoselectivity invokes the enolate anion of 1,3-dihydro-2H-1,4- benzodiazepin-2-one as the reactive species (Scheme 2). Acid-catalyzed hydrolytic ring opening of 3 afforded threo-β-hydroxy-phenylalanine 17, whereas from 4, the N-(benzyloxy)carbonyl derivative 18 of erythro-β- hydroxy-phenylalanine was obtained (Scheme 3); in both cases, neither elimination of H2O from the C(3)-CHOH moiety nor epimerization at C(3) were observed. This result opens a new pathway to various configurationally uniform α-amino-β-hydroxy carboxylic acids and their congeners of biological importance.