152706-23-5

Usage

Uses

Used in Pharmaceutical Industry:
(S)-(1-TRITYLAZIRIDIN-2-YL)METHANOL is used as a building block for the synthesis of various pharmaceuticals due to its unique structure and reactivity. Its chiral nature allows for the creation of enantiomerically pure compounds, which are essential in the development of effective and selective medications.
Used in Organic Synthesis:
In the field of organic chemistry, (S)-(1-TRITYLAZIRIDIN-2-YL)METHANOL is used as an intermediate for the preparation of complex organic molecules. Its trityl group provides a protective function for alcohols, facilitating the synthesis of target molecules with greater ease and precision.
Used in Drug Development:
(S)-(1-TRITYLAZIRIDIN-2-YL)METHANOL holds potential for use in the development of new drugs, particularly in the creation of biologically active molecules. Its unique structure and properties make it a valuable tool in the design and synthesis of novel therapeutic agents.
Used in Research and Development:
(S)-(1-TRITYLAZIRIDIN-2-YL)METHANOL is also utilized in research and development settings, where it can be employed to study the properties and reactivity of aziridine-based compounds. This knowledge can be applied to the design of new synthetic routes and the development of innovative applications in various industries.

Upstream product

• 75154-68-6 methyl (2S)-N-tritylaziridine-2-carboxylate 
• 13515-76-9 methyl N-trityl-L-serinate 
• 76357-12-5 (S)-methyl3-((methylsulfonyl)oxy)-2-(tritylamino)propanoate 

Downstream Products

• 1095273-25-8 [(2S)-1-tritylaziridin-2-yl]methyl methanesulfonate 
• 1198080-11-3 tert-butyl (S)-2-(hydroxymethyl)aziridine-1-carboxylate 
• 20020-75-1 N-tritylprop-2-en-1-amine 
• 236742-93-1 (4R)-E-3-(3,4-methylenedioxyphenyl)-4,5-(N-triphenylmethylepimino)-2-pentenoic acid ethyl ester 
• 236742-92-0 (4R)-Z-3-(3,4-methylenedioxyphenyl)-4,5-(N-triphenylmethylepimino)-2-pentenoic acid ethyl ester 
• 236742-78-2 (2S)-1-(3,4-methylenedioxyphenyl)-2,3-(N-triphenylmethylepimino)-1-propanol 
• 1008128-93-5 (S)-(1-tritylaziridin-2-yl)methyl 4-methylbenzenesulfonate 
• 152706-54-2 1-triphenylmethyl-2-aziridinecarboxaldehyde 

Relevant academic research and scientific papers

COVALENT RAS INHIBITORS AND USES THEREOF

The disclosure features compounds, or pharmaceutically acceptable salts thereof, alone and in combination with other therapeutic agents, pharmaceutical compositions, and protein conjugates thereof, capable of modulating biological processes including Ras, and their uses in the treatment of cancers.

Straightforward synthesis and antioxidant studies of chalcogenoaziridines

Herein we reported the synthesis of chalcogenoaziridines through the introduction of the organoselenium moiety in the aziridine framework through the nucleophilic substitution of the OTs leaving group. In addition, the antioxidant activity, as reflected b

N-Trityl-aziridinyl alcohols as highly efficient chiral catalysts in asymmetric additions of organozinc species to aldehydes

A synthetic route leading to a series of new chiral catalysts containing the N-trityl-aziridine moiety and a primary and a secondary hydroxyl group as nucleophilic centers is described. All the new compounds have been tested as chiral catalysts in the enantioselective addition of diethylzinc and phenylethynylzinc to aryl and alkyl aldehydes, yielding the corresponding chiral alcohols in high chemical yields (up to 96%) and with excellent ee's of ca. 90%. The influence of the stereogenic centers located at the carbon atom bonded with the hydroxyl moiety and on the carbon of the aziridine ring on the stereochemistry of the addition reactions is also discussed.

Synthesis of enantiopure 3-substituted morpholines

Enantiopure 3-substituted morpholines were assembled through ring-opening of a N-2-benzothiazolesulfonyl (Bts) activated aziridine with organocuprates followed by a ring annulation reaction with a vinylsulfonium salt under microwave conditions. Deprotecti

Asymmetrie total syntheses of (-)-renieramycin M and G and (-)-jorumycin using aziridine as a lynchpin

"Chemical Equation Presented" By exploring the triple reactivity of two aziridines and double nucleophilicity of two aromatics, convergent and versatile syntheses of the above four natural products were developed.

Selectively N-protected enantiopure 2,5-disubstituted piperazines: Avoiding the pitfalls in solid-phase Fukuyama-Mitsunobu cyclizations

An efficient solid-phase route to ring-substituted piperazines from O-linked resin-bound (S)-aziridine-2-methanol is described. Regioselective microwave-assisted aminolysis followed by intramolecular FukuyamaMitsunobu cyclization constitute the key features of the protocol. Simple piperazines and diazepanes were readily obtained without preceding N-protection of the acyclic intermediate, whereas attempts to extend this protocol to chiral 2,5-disubstituted piperazines failed. Modifications encompassing N-carbamoylation prior to ring-closure were therefore investigated. However, standard carbamoylating agents, for example, Fmoc-Cl and Alloc-Cl tended to give bis-protected by-products. Thus, novel microwave-assisted solid-phase N-protection procedures were developed for efficient introduction of Fmoc, Boc and Alloc groups. The subsequent cyclization proceeded in moderate to excellent yields depending on the bulk of the side chain and type of N-protecting group. This protocol readily provided novel cis- and trans-2,5-disubstituted piperazines displaying a variety of N-protecting group patterns after further on-resin manipulations. Also, unexpected by-products obtained during these optimization studies were identified and characterized. This includes nosylated ureas arising from an alternative cyclization pathway. Finally, post-cleavage oxidation gave access to the Fmoc/Boc-protected a-amino acid as well as the corresponding aldehyde. The chiral piperazines described in this work will enable construction of combinatorial libraries with a higher chemical diversity compared to those containing simple N.N′-difunctionalized piperazines, often present in drug-like compounds.

An enantiospecific approach to triazolylalanine derivatives

An efficient and practical route to an enantiomerically pure aziridinylmethyl azide is described that can be transformed to the corresponding triazole by a copper-catalysed [3+2] alkyne cycloaddition reaction. The transformation of these intermediates int

First synthesis of N-[(aziridin-2-yl)methyl]benzimidazolequinone and analysis of toxicity towards normal and Fanconi anemia cells

A diazole is N-substituted with 1-trityl-2-methylaziridine and demethylated and oxidised with NBS under acidic conditions to give a benzimidazolequinone; this novel anti-tumour agent is marginally more cytotoxic than mitomycin C (MMC) towards the normal h

Preparation of alkyl-substituted indoles in the benzene portion. Part 9. Synthesis of (1aS,8bS)-1-tert-butyloxycarbonyl-8-formyl-1,1a,2,8b-tetrahydroazirino [2',3':3,4]pyrrolo[1,2-a]indole. Model study for the enantiospecific synthesis of ziridinomitosenes

Effective pathways for an enantiospecific synthesis of (1aS,8bS)-1-tert-butyloxycarbonyl-8-formyl-1,1a,2,8b-tetrahydroazirino [2',3':3,4]pyrrolo[1,2-a]indole (8) were investigated as a preliminary experiment aiming at chiral syntheses of aziridinomitosenes 5 and (1aS,8bS)-8-[[(aminocarbonyl)oxy]methyl]-5-formyl-7-hydroxy-1,1a,2,8b- tetrahydroazirino[2',3':3,4]pyrrolo[1,2-a]indole (6a). An aldehyde 14, derived from L-serine was condensed with 2-lithio-1-(phenylsulfonyl)indole (10) to afford diastereomers 15a and 15b, whose stereochemistry was unambiguously determined by 1H-NMR studies of the 1,3-dioxane derivatives 17a, 17b, and 18 as well as the X-ray crystallographic analysis of a dihydropyrrolo[1,2-a]indole derivative 31a. The latter compound was prepared from 15a via the following operations (Chart 5): (i) removal of the acetonide and the indole-protecting groups, followed by acetylation to form 29a, (ii) Vilsmeier reaction to produce 30a, and (iii) hydrolysis of acetyl groups, partial methanesulfonylation (mesylation), and treatment with potassium carbonate in acetonitrile. A diastereomer 31b was obtained from 15b in a similar manner. Both isomers 31a and 31b afforded the desired compound 8 upon treatment with a mesylation reagent followed by potassium tert-butoxide in tetrahydrofuran.