115887-83-7

Upstream product

• 75266-40-9 N-benzyloxycarbonyl-L-α-vinylglycine methyl ester 
• 501-53-1 benzyl chloroformate 
• 75266-39-6 methyl (S)-2-<<(benzyloxy)carbonyl>amino>-4-(methylsulfinyl)butanoate 
• 56762-93-7 methyl (S)-2-(benzyloxycarbonylamino)-4-methylmercaptobutanoate 

Downstream Products

• 115764-12-0 2-benzyloxycarbonylamino-2-deoxy-D-threonamide 
• 115764-15-3 2-benzyloxycarbonylamino-3,4-di-O-chloroacetyl-2-deoxy-D-threonamide 
• 115764-16-4 2-benzyloxycarbonylamino-2-deoxy-4-O-trityl-D-threonamide 
• 115764-17-5 2-benzyloxycarbonylamino-2-deoxy-3-O-mesyl-4-O-trityl-D-threonamide 
• 115764-22-2 (Z)-2-benzyloxycarbonylamino-4-trityloxybut-2-enamide-N-sulphonic acid tetrabutylammonium salt 
• 115764-19-7 2-benzyloxycarbonylamino-2-deoxy-3-O-mesyl-4-O-trityl-D-threonamide-N-sulphonic acid tetrabutylammonium salt 

Relevant academic research and scientific papers

Synthesis of new 3- and 4-substituted analogues of acyl homoserine lactone quorum sensing autoinducers

The quorum sensing mechanism in Gram-negative bacteria uses small intercellular signal molecules, N-acyl-homoserine lactones (AHLs), to control transcription of specific genes in relation to population density. In this communication, we describe the parallel synthesis of new AHL analogues, in which substituents have been introduced into the 3- and 4-positions of the lactone ring. These analogues have been screened for their ability to activate and inhibit a Vibrio fischeri LuxI/LuxR-derived quorum sensing reporter system.

Enantioselective Synthesis of (3S)-trans-4-(Substituted Methyl)monobactams from 2,3-O-Isopropylidene-D-glyceraldehyde

The enantioselective synthesis of various (3S)-trans-4-(substituted methyl)-2-oxoazetidine-1-sulphonic acid derivatives from 2,3-O-isopropylidene-D-glyceraldehyde is described.Reaction of this aldehyde with trimethylsilyl cyanide gave a 80:20 ratio of the corresponding threo and erythro α-amino-nitriles, which by amino protection and subsequent treatment with basic hydrogen peroxide provided the corresponding α-amino carboxamides.Successive selective protection, activation, sulphonation and, finally, stereospecific cyclization of the threo α-carboxamide yielded (2S,4R)-3-benzyloxycarbonylamino-4-hydroxymethyl-2-oxoazetidine-1-sulphonic acid, an intermediate for the synthesis of the corresponding 4-acyloxymethyl-, 4-carbamoyloxymethyl-, 4-methylsulphonyloxy-methyl-, 4-iodomethyl-, and 4-methyl-2-oxozetidines.