74481-56-4

Upstream product

• 74491-51-3 O-tosyl-N-tritylthreonine methyl ester 
• 74481-55-3 methyl (2S,3R)-3-hydroxy-2-triphenylmethylaminobutanoate 
• 76-83-5 trityl chloride 

Downstream Products

• 167502-57-0 (2S,3S)-2-hydroxymethyl-3-methyl-1-(triphenylmethyl)aziridine 
• 83824-81-1 (2S,3S)-3-methylaziridine-1,2-dicarboxylic acid 1-benzylester 2-methyl ester 
• 167226-25-7 [(2S,3S)-3-methylaziridin-2-yl](diphenyl)methanol 
• 908293-54-9 (2S,3S)-3-methylaziridin-2-yl(bis(4-methoxyphenyl))methanol 
• 1182716-18-2 C₁₈H₁₅F₆NO 
• 1182716-26-2 C₁₈H₂₁NO₃ 
• 1182716-22-8 C₁₆H₁₅F₂NO 
• 1182716-25-1 C₁₈H₂₁NO 
• 1182716-16-0 C₁₈H₁₅F₆NO 
• 1182716-20-6 C₁₆H₁₅F₂NO 
• 73984-43-7 (2S,3S)-1-trityl-3-methyl-2-aziridinecarbonyl-D-valylproline t-butyl ester 
• 193635-06-2 (2S,3S)-3-Methyl-1-[(2S,3S)-3-methyl-1-(toluene-4-sulfonyl)-aziridine-2-carbonyl]-aziridine-2-carboxylic acid methyl ester 
• 153451-34-4 ((S)-1-Methyl-allyl)-trityl-amine 

Relevant academic research and scientific papers

Studies on the synthesis of orthogonally protected azalanthionines, and of routes towards β-methyl azalanthionines, by ring opening of N-activated aziridine-2-carboxylates

Orthogonally protected azalanthionines were successfully synthesised by the ring-opening of N-activated aziridine-2-carboxylates with protected diaminopropanoic acids (DAPs). The required DAPs were also prepared by ring-opening of N-activated aziridine-2-carboxylates with para- methoxybenzylamine, but it was found that the choice of aziridine protecting groups dictated both the success of the reaction as well as the regioselectivity of the isolated products. Attempts to extend the methodology to the preparation of the more sterically demanding β-methyl azalanthionines have, so far, been unsuccessful.

Synthesis of α-amino acids by reaction of aziridine-2-carboxylic acids with carbon nucleophiles

A variety of homochiral α-amino acids have been prepared in good yield via regioselective reaction of higher order cuprates with (2S)-N-para-toluenesulfonylaziridine-2-carboxylic acid 4. The reaction was much less regioselective and low yielding when higher order cuprates were reacted with the more hindered aziridine carboxylic acid 30, the principal products being protected β-amino acids. Reaction of lithium trimethylsilylacetylide with the aziridine acid 30, however, gave a protected α-amino acid which was converted to the protected isoleucine ester 37. The Royal Society of Chemistry 2006.

Total synthesis of trunkamide A, a novel thiazoline-based prenylated cyclopeptide metabolite from Lissoclinum sp.

Full details of a total synthesis of the doubly prenylated cyclic peptide trunkamide A of marine origin, and also its C45 epimer, are described.

Solution- and solid-phase synthesis of 4-hydroxy-4,5-dihydroisoxazole serivatives from enantiomerically pure N-tosyl-2,3-aziridine alcohols

(formula presented) Enantiomerically pure N-tosyl-2,3-aziridine alcohols are directly converted into 4-hydroxy-4,5-dihydroisoxazole 2-oxides through oxidation to the corresponding aldehydes followed by in situ tandem nitroaldol-intramolecular cyclization.

Synthesis of natural and non natural orthogonally protected lanthionines from N-tritylserine and allo-threonine derivatives

The reactivity of electrophiles derived from N-tritylserine, threonine and allothreonine esters toward a selection of nucleophiles was investigated. Best yields from substitution products were obtained with N-trityliodoalanine and soft nucleophiles such a

Synthesis and crystal structure of enantiopure N-tritylaziridin-2-yl-methanols from L-serine and L-threonine

A convenient multigram 'one pot procedure' for the synthesis of methyl N-tritylaziridine-2-carboxylates 1 and 2, starting from the N-tritylmethyl esters of L-serine 9 and L-threonine 10 and using methanesulfonyl chloride and triethylamine, is described. T

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,

Studies on 2-Aziridinecarboxylic Acid.IV.Total Synthesis of Actinomycin D (C1) via Ring-opening Reaction of Aziridine

Actinomycin D (C1) has been synthesized by a route involving the ester formation between two peptide fragments, (2S,3S)-1-(2-nitro-3-benzyloxy-4-methylbenzoyl)-3-methyl-2-aziridiecarbonyl-D-valylproline t-butyl ester and N-benzyloxycarbonylsarc