329912-53-0

Upstream product

• 911225-55-3 (2S,4R)-2-amino-4-[(tert-butyldiphenylsilyloxy)methyl]-4-butanolide 
• 104241-32-9 (2S,4R)-2-tert-butoxycarbonylamino-4-hydroxymethyl-4-butanolide 
• 135582-85-3 (2S,4R)-2-tert-butoxycarbonylamino-4-azidomethyl-4-butanolide 
• 850996-92-8 (2S,4R)-1-hydroxy-4-triisopropylsilanyloxy-5-benzyloxycarbonylaminopent-2-ylaminocarboxylic acid tert-butyl ester 
• 128427-09-8 (S)-N-tert-butoxycarbonyl-aspartic acid diethyl ester 
• 147959-18-0 (4S)-2,2-dimethyl-4-(2-hydroxyethyl)oxazolidine-3-carboxylic acid tert-butyl ester 
• 147959-19-1 (4S)-2,2-dimethyl-3-(t-butoxycarbonyl)-4-(formylmethyl)-1,3-oxazolidine 
• 371972-14-4 tert-butyl-(2S,4R)-N^α-(tert-butoxycarbonyl)-N^δ-(benzyloxycarbonyl)-4-hydroxy-ornithinate 
• 1138-80-3 N-(Benzyloxycarbonyl)glycine 
• 2899-57-2 Sphenyl N-benzyloxycarbonylaminoethanothioate 
• 630400-90-7 (R)-5-((S)-2-Amino-2-tert-butoxycarbonyl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester 
• 128427-10-1 (S)-2-(tert-butoxycarbonylamino)-1,4-butanediol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 850996-90-6 (4S)-[(2R)-3-benzyloxycarbonylamino-2-triisopropylsilanyloxypropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 

Downstream Products

• 135582-94-4 (R)-3-benzyloxycarbonyl-5-<(S)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)ethyl>-2,2-dimethyl-1,3-oxazolidine 
• 911225-68-8 methyl (2S,4R)-5-benzyloxycarbonylamino-2-tert-butoxycarbonylamino-4-hydroxypentanoate 

Relevant academic research and scientific papers

Antibacterial amide macrocycles

The invention relates to antibacterial amide macrocycles, to methods for the production thereof, and to the use of the same for producing pharmaceuticals for the treatment and/or prophylaxis of illness, especially bacterial infections.

First synthesis of polyoxin M

Chiral enolate derived from (4R)-4-tert-butyldiphenylsilyloxymethyl-4-butanolide 10 with lithium hexamethyldisilyazide (LiHMDS) was treated with trisyl azide, followed by addition of TMSCl to give (2S,4R)-2-azido-4-[(tert-butyldiphenylsilyloxy)methyl]-4-b

IMPROVED PROCEDURE FOR THE PREPARATION OF (4S)- OR (4R)-2,2-DIMETHYL-4-(2-HYDROXETHYL)OXAZOLIDINE-3-CARBOXYLIC ACID ALKYL ESTERS

The present invention is directed to a process for the preparation of (4S)- or (4R)-2,2-dimethyl-4-(2-hydroxethyl)oxazolidine-3-carboxylic acid alkyl esters. The invention is further directed to an intermediate product from which those alkyl esters may be obtained.

Highly efficient approach to orthogonally protected (2S,4R)- and (2S,4S)-4-hydroxyornithine

(Chemical Equation Presented) A concise stereoselective approach to both orthogonally protected (25,4A)- and (2S,4S)-4-hydroxyornithine, key constituents of the biphenomycin-and clavalanine-type antibiotics, respectively, has been developed. The approach is based on bis(oxazoline) copper(II)-complex-catalyzed diastereoselective Henry reactions of nitromethane with the homoserine-derived aldehyde 6. The synthesis of this versatile chiral building block has been markedly improved.

Asymmetric synthesis of orthogonally protected (2S,4R)- and (2S,4S)-4-hydroxyornithine

Synthesis of orthogonally protected (2S, 4R)- and (2S, 4S)-4-hydroxyornithine was reported featuring an asymmetric alkylation of N-(diphenylmethylene)glycine tert-butyl ester (6) by (5S)-N-benzyloxycarbonyl-5-iodomethyl oxazolidine (7). Double stereoselection was examined using chiral ammonium salts as phase transfer catalysts and a substrate-directed chiral induction is documented.

Synthesis of a 3-aminopiperidin-2,5-dione as a conformationally constrained surrogate of the Ala-Gly dipeptide

The preparation of the Boc-{Ala-Gly}-OBn pseudopeptide 4 is reported. The key intermediate, aminoester 5b, was obtained by a cross-coupling reaction of alaninezinc iodide 6 and the thioester of glycine 9.