78688-64-9

Upstream product

• 21691-50-9 Ala-OtBu 
• 100-52-7 benzaldehyde 
• 13404-22-3 tert-butyl L-alaninate hydrochloride 

Downstream Products

• 78738-80-4 1-<(S)-1-(tert-butoxycarbonyl)ethyl>-(3R,4S)-3-azido-4-phenylazetidin-2-one 
• 78688-66-1 1-<(S)-1-(tert-butoxycarbonyl)ethyl>-(3S,4R)-3-azido-4-phenylazetidin-2-one 
• 98463-80-0 (3S,4R)-1-<(S)-1-(tert-butoxycarbonyl)-ethyl>-3-(benzyloxy)-4-phenylazetidin-2-one 
• 98380-70-2 (3R,4S)-1-<(S)-1-(tert-butoxycarbonyl)-ethyl>-3-(benzyloxy)-4-phenylazetidin-2-one 
• 147714-90-7 (R)-2-amino-2-methyl-3-phenylpropanoic acid tert-butyl ester 
• 120346-40-9 (S)-2-Methyl-2-[(3R,4S)-2-oxo-3-(2-oxo-4-phenyl-oxazolidin-3-yl)-4-phenyl-azetidin-1-yl]-3-phenyl-propionic acid tert-butyl ester 
• 120346-41-0 (R)-phenylalanyl-(S)-α-methylphenylalanine 
• 120346-39-6 (S)-2-[(3R,4S)-2-Oxo-3-((R)-2-oxo-4-phenyl-oxazolidin-3-yl)-4-phenyl-azetidin-1-yl]-propionic acid tert-butyl ester 
• 98380-65-5 [(2S,3S)-1-((S)-1-Benzyloxymethyl-3-methyl-butyl)-2-phenyl-azetidin-3-yl]-[(S)-2-((2S,3S)-3-benzyloxy-2-phenyl-azetidin-1-yl)-propyl]-amine 
• 136693-57-7 (2S,3S)-1-<(S)-2-hydroxy-1-methylethyl>-2-phenyl-3-(benzyloxy)azetidine 
• 136778-86-4 (2R,3R)-1-<(S)-2-hydroxy-1-methylethyl>-2-phenyl-3-(benzyloxy)azetidine 
• 136693-83-9 (2R,5S)-1-phenyl-2-hydroxy-5-methyl-7-oxa-4-azaheptane 
• 136693-84-0 (2S,5S)-1-phenyl-2-hydroxy-5-(hydroxymethyl)-7-methyl-4-azaheptane 
• 98380-60-0 (3S,4R)-1-<(S)-1-<(benzyloxy)methyl>-3-methylbutyl>-3-<(S)-2-<(3'R,4'S)-3'-(benzyloxy)-2'-oxo-4'-phenylazetidin-1'-yl>propanoyl>-4-phenylazetidin-2-one 

Relevant academic research and scientific papers

Substituted Pyrrolidines and Methods of Use

The invention discloses compounds of Formula (I) wherein R1, R2, R2A, R3, R3A, R4, R4A, and R5 are as defined herein. The present invention relates to compounds and their use in the treatment of cystic fibrosis, methods for their production, pharmaceutical compositions comprising the same, and methods of treating cystic fibrosis by administering a compound of the invention.

Asymmetric alkylation catalyzed by chiral alkali metal alkoxides of TADDOL. Synthesis of α-methyl amino acids

It is shown that sodium alkoxides formed from (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-bis(diphenylmethanol) ((R,R)-TADDOL) and some of its derivatives can be used as chiral catalysts for enantioselective alkylation of Schiff's bases derived from alanine with reactive alkyl halides. Acid hydrolysis of the reaction products affords (R)-α-methytphenyl-alanine, (R)-α-allylalanine, and (R)-α-methylnaphthylalanine in 61-93% yields and with ee 69-94%. When (S,S)-TADDOL is used, the (3)-amino acid is formed. A mechanism explaining the observed features of the reaction is proposed.

Remarkable Effects of Lone Pair-Lone Pair Interactions on the Extremely Stereoselective Cycloaddition of Azidoketene to Chiral 3-Imino-β-lactams

The stereoselective cycloaddition of azidoketene to cis-3-imino-β-lactams 1, 2, and 3, trans-3-imino-β-lactam 4, and cis-3-iminoazetidine 5 were carried out.It was found that the reactions of 1, 2, and 3 proceeded with > 99.5 percent stereoselectivity to give bis-β-lactams 9, 14, and 19, respectively.The reaction of 4 gave a bis-β-lactam 20 with 62 percent de, and the reaction of 5 gave a β-lactamazetidine 21 with 32 percent de including the asymmetry in the opposite direction.These results clearly indicate that, in addition to the conventional steric effects, the lone pair-lone pair interaction of β-lactam oxygen with the intermediate betaine's oxygen is the crucial factor for the extremely stereoselective cycloaddition of azidoketene to 1, 2, and 3.Possible mechanisms for these stereoselective cycloadditions are proposed.The X-ray crystal structure of 3a and the calculated energy-minimum conformations of 3a, 4, and 5 with MODEL-MM2-ROTOCHEM programs are provided.

Effective Method for the Asymmetric Synthesis of Bis-β-lactams by the Cycloaddition of Azidoketen to Benzylideneamines Bearing a Chiral β-Lactam Backbone

Extremely high stereoselectivity was observed in the asymmetric cycloaddition of azidoketen to 1--3-benzylideneamino-4-phenylazetidin-2-ones, which gave rise to the formation of optically pure bis-β-lactams.