85550-09-0

Basic information

• Product Name: (2R,3R)-1-trityl-3-methyl-2-aziridinecarboxylic acid methyl ester
• Synonyms: (2R,3R)-1-trityl-3-methyl-2-aziridinecarboxylic acid methyl ester
• CAS NO: 85550-09-0
• Molecular Weight: 357.452
• Mol File: 85550-09-0.mol

Chemical Properties

• CAS DataBase Reference: (2R,3R)-1-trityl-3-methyl-2-aziridinecarboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R)-1-trityl-3-methyl-2-aziridinecarboxylic acid methyl ester(85550-09-0)
• EPA Substance Registry System: (2R,3R)-1-trityl-3-methyl-2-aziridinecarboxylic acid methyl ester(85550-09-0)

Safety Data

• Hazardous Substances Data: 85550-09-0(Hazardous Substances Data)

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 85482-79-7 N-trityl-D-threonine methyl ester 
• 76-83-5 trityl chloride 
• 85482-83-3 (2R,3S)-3-Methanesulfonyloxy-2-(trityl-amino)-butyric acid methyl ester 

Downstream Products

• 85482-80-0 S-benzoyl-N-benzyloxycarbonyl-threo-3-methyl-D-cysteine methyl ester 
• 425399-95-7 2-benzyloxycarbonylamino-3-benzylsulfanyl-butyric acid methyl ester 
• 858669-61-1 (2S,3S)-N-benzyloxycarbonyl-3-methylcysteine methyl ester 
• 85550-10-3 (2R,3R)-1-benzyloxycarbonyl-3-methyl-2-aziridinecarboxylic acid methyl ester 
• 60027-61-4 methyl (2Z)-2-(N-benzyloxycarbonylamino)but-2-enoate 
• 858669-60-0 (2S,3S)-2-Benzyloxycarbonylamino-3-tritylsulfanyl-butyric acid methyl ester 
• 858669-59-7 (2S,3S)-2-Benzyloxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-butyric acid methyl ester 

Relevant articles and documents

Scalable synthesis of orthogonally protected β-methyllanthionines by indium(III)-mediated ring opening of aziridines

Lantibiotics are a class of peptide antibiotics with activity against most Gram-positive bacteria. Lanthionine (Lan) and β-MeLan are unusual thioether-bridged, non-proteinogenic amino acids, which are characteristic features of lantibiotics. In this paper, we report the facile stereoselective synthesis of β-methyllanthionines with orthogonal protection by nucleophilic ring opening of aziridines. This method leads to an expedient access to β-methyllanthionines and allows production of over 30 g of β-methyllanthionine in a single batch.

Versatile and stereoselective syntheses of orthogonally protected β-methylcysteine and β-methyllanthionine

(Chemical Equation Presented) Lantibiotics are a class of lanthionine (and/or β-methyllanthionine)-containing peptides with antibioitic activity against Gram-positive bacteria. As part of our research effort directed toward the synthesis and mechanistic s

Biomimetic stereoselective formation of methyllanthionine.

Fmoc-(2R,3S)-3-methyl-Se-phenylselenocysteine was used for the synthesis of dehydrobutyrine (Dhb)-containing peptides. Biomimetic cyclization via Michael addition of Cys to a Dhb yielded the B-ring of the lantibiotic subtilin as a single diastereomer. The methyllanthionine product was shown to have the natural configuration by preparation of the authentic stereoisomer. The formation of a single isomer suggests that the prepeptide has a strong intrinsic preference for the stereochemistry observed in lantibiotics. [reaction: see text]

Asymmetric Ketone Reduction using Chiral Oxazaborolidines derived from Aziridine Carbinols

Asymmetric borane reduction of acetophenone using 1,3,2-oxazaborolidines derived from aziridine-2-tertiary alcohols 1 and 2 yielded the corresponding alcohol in high optical yields.The synthesis of the novel chiral catalysts 1 and 2 using D-and L-serine,

Synthesis of threo-3-Methylcysteine from Threonine

threo-3-Methyl-D-cysteine as a moiety of β-methyllanthionine in the peptide antibiotic nisin was synthesized stereospecifically.The reaction of (2R,3R)-3-methyl-2-aziridinecarboxylic acid derivative prepared from D-threonine with thiobenzoic acid gave the