10068-52-7

Usage

Uses

Used in Pharmaceutical Industry:
N-[(BENZYLOXY)CARBONYL]-3,3,3-TRIFLUOROALANINE is used as a key intermediate in the synthesis of 3,3,3-Trifluoroalanine and its derivatives. It serves as a building block for the development of novel pharmaceutical compounds with potential therapeutic applications.
Used in Peptide Synthesis:
In the field of peptide chemistry, N-[(BENZYLOXY)CARBONYL]-3,3,3-TRIFLUOROALANINE is used as a protected amino acid for the synthesis of 3,3,3-Trifluoroalanyl peptides. The benzyloxycarbonyl group protects the amino group during peptide bond formation, allowing for selective deprotection and further modifications to create bioactive peptides with specific functions.

Upstream product

• 96105-72-5 3,3,3-trifluoroalanine hydrochloride 
• 501-53-1 benzyl chloroformate 
• 817164-27-5 N-benzyloxycarbonyl-1,1,1-trifluoro-4-(p-tolyl)-3-buten-2-amine 
• 276862-99-8 (2S,3S)-2-benzyloxycarbonyl[N-(toluene-4-thio)amino]-3-trifluoroacetoxy-2-trifluoromethylbutyric acid methyl ester 
• 17463-43-3 3,3,3-trifluoro-DL-alanine 
• 27240-49-9 2-benzyloxycarbonylamino-3,3,3-trifluoropropionic acid methyl ester 
• 26208-11-7 N-(trifluoromethyl-2-propyl)carbamic acid benzyl ester 

Downstream Products

• 27414-80-8 3,3,3-Trifluor-N-benzyloxycarbonyl-DL-alanyl-glycin-methylester 
• 27240-45-5 3,3,3-Trifluor-N-benzyloxycarbonyl-alanin-tert.-butylester 
• 177469-13-5 (-)-(2R)-N-benzyloxycarbonyl-3,3,3-trifluoroalanine 
• 27240-49-9 2-benzyloxycarbonylamino-3,3,3-trifluoropropionic acid methyl ester 

Relevant academic research and scientific papers

Methyl to trifluoromethyl substitution as a strategy to increase the membrane permeability of short peptides

Here, we investigated the effect of CH3to CF3substitution on the membrane permeability of peptides. We synthesized a series of peptides with CF3groups and corresponding nonfluorinated peptides and measured the membrane per

POLYCYCLIC TLR7/8 ANTAGONISTS AND USE THEREOF IN THE TREATMENT OF IMMUNE DISORDERS

The present invention relates to compounds of Formula (I) and pharmaceutically acceptable compositions thereof, useful as toll-like receptor 7/8 (TLR7/8) antagonists. In Formula (I), Ring A is aryl or heteroaryl; Ring B is aryl or heteroary; and X is C(R4)2, O, NR4, S, S(R4), or S(R4)2.

Preparation of fluoroalkyl imines, amines, enamines, ketones, α-amino carbonyls, and α-amino acids from primary enamine phosphonates

A simple method for preparation of fluoroalkyl β-enaminophosphonates 1 from alkylphosphonates 2 and perfluoroalkyl nitriles 3 is reported. Olefination reaction of functionalized phosphates 1 with aldehydes gives α,β-unsaturated imines 5. Acid hydrolysis of these fluoroalkyl derivatives 5 affords α,β-unsaturated ketones 6, while their selective reduction with hydrides leads to the formation of allylamines 7, enamines 8, and saturated ketones 9 or amines 10. Selective oxidative cleavage of the carbon-carbon double bond of allylamines 7 gives fluorinated α-amino aldehydes 12, α-amino ketones 13, or α-amino acid derivatives 14.

The 'non-oxidative' Pummerer reaction: Conclusive evidence for S(N)2- type stereoselectivity, mechanistic insight, and synthesis of enantiopure L- α-trifluoromethylthreoninate and D-α-trifluoromethyl-allo-threoninate

Enantiopure methyl D-α-trifluoromethyl-allo-threoninate 18 and L-α- trifluoromethylthreoninate 19 were synthesized using (R)-ethyl p- tolylsulfoxide as chiral α-hydroxyethyl anion equivalent. The key step was the S(N)2-type replacement of the sulfinyl auxiliary with a hydroxy group, via trifluoroacetic anhydride promoted 'non-oxidative' Pummerer reaction (NOPR) of the diastereomeric intermediate β-sulfinyl amines 14 and 15, obtained by condensation of (R)-ethyl p-tolylsulfoxide 13 with the N-Cbz imine of methyl trifluoropyruvate 12. The conclusive evidence for S(N)2-type stereoselectivity of the NOPR was achieved by X-ray diffraction of both the starting diastereomer 14 and the p-bromobenzoate 25, obtained from the threoninate 19. NMR monitoring of the NOPR performed on 15 allowed the detection of a transient intermediate, which was identified as the four membered cyclic σ-sulfurane 27. This intermediate spontaneously rearranged (40 min, rt) into the corresponding sulfenamide 17, probably via an intramolecular displacement of the sulfinyl by a trifluoroacetoxy group, with inversion of configuration at the carbon stereocenter. The same process occurred for the diastereomeric β-sulfinyl amine 14, but the sulfenamide 16 was formed at very fast rate, thus precluding NMR detection of the corresponding σ-sulfurane intermediate 26. One-pot treatment of the diastereomeric sulfenamides 16 and 17 with NaBH4 afforded very good yields of the corresponding threoninates 18 and 19.