86122-64-7

Upstream product

• 142941-66-0 benzyl (2S,3S)-3-methyl-1-trityl-aziridine-2-carboxylate 
• 142941-67-1 (2S,3R)-3-(Toluene-4-sulfonyloxy)-2-(trityl-amino)-butyric acid benzyl ester 
• 501-53-1 benzyl chloroformate 
• 142941-65-9 N-trityl-L-threonine benzyl ester 
• 86123-06-0 benzyl (2S,3S)-1-H-3-methyl-2-aziridinecarboxylate 

Downstream Products

• 669089-96-7 (2S,3R)-2-Benzyloxycarbonylamino-3-((2R,3S,4R,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylmethoxy)-butyric acid benzyl ester 

Relevant academic research and scientific papers

Aziridine ring opening as regio- and stereoselective access to O-glycosyl amino acids and their transformation into O-glycopeptide mimetics

Glycosyl amino acid mimetics of the typical GalNAc-(1→O)-Ser/Thr motif of O-glycopeptides were synthesised. Starting from galactose a 1,5-anhydro derivative could be obtained and regio- and stereoselectively coupled to serine- or threonine-derived aziridine compounds, respectively. The corresponding Fmoc derivatives could be used to prepare two 13-mer glycopeptides of the mucin MUC1 carrying instead of Ser-2 or Th-5, the corresponding O-glcycosyl amino acid mimetics.

One-step synthesis of optically active benzyl N-trityl-L-aziridine-2-carboxylic esters

Benzyl N-trityl-L-serine or threonine esters give upon treatment with sulphuryl chloride the corresponding benzyl (2s)-1-trityl-2-aziridine carboxylate or (2S, 3S)-1-trityl-3-methyl-2-aziridinecarboxylate esters in excellent yields.

Studies on 2-Aziridinecarboxylic Acid. IX. Convenient Synthesis of Optically Active S-Alkylcysteine, threo-S-Alkyl-β-methylcysteine, and Lanthionine Derivatives via the Ring-opening Reaction of Aziridine by Several Thiols

A convenient synthesis of optically active S-alkylcysteine, threo-S-alkyl-β-methylcysteine, and lanthionine derivatives has been investigated.Benzyl 1-benzyloxycarbonyl-(2S)-2-aziridinecarboxylate and benzyl (2S,3S)-1-benzyloxycarbonyl-3-methyl-2-aziridin