152706-54-2

Upstream product

• 75154-68-6 methyl (2S)-N-tritylaziridine-2-carboxylate 
• 152706-23-5 (S)-N-triphenylmethyl-aziridinylmethanol 

Downstream Products

• 236742-78-2 (2S)-1-(3,4-methylenedioxyphenyl)-2,3-(N-triphenylmethylepimino)-1-propanol 

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.

Investigation of a flexible enantiospecific approach to aziridines

(Chemical Equation Presented) A flexible approach to functionalized and enantioenriched aziridines has been developed from an intermediate aziridinylmethyl tosylate. This protocol features a Cu-catalyzed Grignard substitution reaction that allows a range of functionalized organic fragments to be incorporated. Moreover, a convenient one-pot procedure is outlined that allows the trityl group to be exchanged for a range of common N-protecting groups.

Baylis-Hillman reaction of N-trityl aziridine-2-(S)-carboxaldehyde

N-Trityl aziridine-2-(S)-carboxaldehyde 1 undergoes a facile Baylis- Hillman reaction with a variety of activated vinyl compounds in the presence of a catalytic amount of DABCO to furnish the corresponding adducts 2 in good yields. Unexpectedly, acetylati

Synthesis of optically active N-allyl amino compounds with defined trisubstituted double bonds

Optically active acyclic N-allylamino compounds with defined configurated trisubstituted double bonds were generated via a three step sequence. The first crucial step was a two-carbon chain elongation of chiral α-aminoacid esters succeeding in a Claisen ester condensation with acetic acid ester enolates. The so formed β-ketoesters were subjected to a one pot procedure of an enol trifluoromethanesulfonate generation and a consecutive palladium catalysed cross-coupling: A Stille or a Sonogashira type reaction allowed to generate selectively the trisubstituted E-olefins.

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.