100841-19-8

Upstream product

• 18598-80-6 methyl N-trityl-(S)-phenylalaninate 
• 47672-25-3 N-trityl-L-phenylalanine 
• 63-91-2 L-phenylalanine 
• 76-83-5 trityl chloride 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 3182-95-4 L-Phenylalaninol 
• 93266-75-2 C₃₄H₂₈N₄O₂ 
• 92176-58-4 Trityl-L-phenylalanylbenzotriazolylester 

Downstream Products

• 74808-00-7 (S)-1-phenylbut-3-yn-2-amine 
• 107591-62-8 [(S)-2-Hydroxy-4-phenyl-3-(trityl-amino)-butyl]-phosphonic acid dimethyl ester 
• 107591-65-1 (4S,5S)-5-<(dimethylphosphinyl)methyl>-4-(phenylmethyl)oxazolidin-2-one 
• 107591-64-0 (4S,5R)-5-<(dimethylphosphinyl)methyl>-4-(phenylmethyl)oxazolidin-2-one 
• 144422-98-0 Cbz-Phe-Pheψ-Gly-OH 
• 144422-97-9 Cbz-Phe-Pheψ-Glycinol 
• 144422-96-8 (2S)-1-phenyl-2-aminotrityl-3-hexen-6-ol 
• 144422-94-6 (2S,3RS)-1-phenyl-2-aminotrityl-1-penten-3-ol 
• 484051-37-8 (2R,1'S)-N-(1'-benzyl-prop-2'-enyl)-N-[(2,4-dimethoxyphenyl)methyl]-2-isopropyl-but-3-enamide 
• 484051-41-4 (3R,6S)-N-[(2,4-dimethoxyphenyl)methyl]-3-isopropyl-6-benzyl-3,6-dihydro-2-pyridone 
• 484051-52-7 (3R,6S)-3-isopropyl-6-benzyl-2-ethoxy-3,6-dihydropyridine 

Relevant academic research and scientific papers

Peptidotriazolamers Inhibit Aβ(1–42) Oligomerization and Cross a Blood-Brain-Barrier Model

In peptidotriazolamers every second peptide bond is replaced by a 1H-1,2,3-triazole. Such foldamers are expected to bridge the gap in molecular weight between small-molecule drugs and protein-based drugs. Amyloid β (Aβ) aggregates play an important role in Alzheimer's disease. We studied the impact of amide bond replacements by 1,4-disubstituted 1H-1,2,3-triazoles on the inhibitory activity of the aggregation “hot spots” K16LVFF20 and G39VVIA42 in Aβ(1–42). We found that peptidotriazolamers act as modulators of the Aβ(1–42) oligomerization. Some peptidotriazolamers are able to interfere with the formation of toxic early Aβ oligomers, depending on the position of the triazoles, which is also supported by computational studies. Preliminary in vitro results demonstrate that a highly active peptidotriazolamer is also able to cross the blood-brain-barrier.

Hydrogen-Borrowing Alkylation of 1,2-Amino Alcohols in the Synthesis of Enantioenriched γ-Aminobutyric Acids

For the first time we have been able to employ enantiopure 1,2-amino alcohols derived from abundant amino acids in C?C bond-forming hydrogen-borrowing alkylation reactions. These reactions are facilitated by the use of the aryl ketone Ph*COMe. Racemisation of the amine stereocentre during alkylation can be prevented by the use of sub-stoichiometric base and protection of the nitrogen with a sterically hindered triphenylmethane (trityl) or benzyl group. The Ph* and trityl groups are readily cleaved in one pot to give γ-aminobutyric acid (GABA) products as their HCl salts without further purification. Both steps may be performed in sequence without isolation of the hydrogen-borrowing intermediate, removing the need for column chromatography.

N-[4-phenyl-3-(benzoylamino)-1,1,1-trifluoro-butyl-2-yl]-phenylalaninol derivative as well as preparation method and application thereof

The present invention discloses an N-[4-phenyl-3-(benzoylamino)-1,1,1-trifluoro-butyl-2-yl]-phenylalaninol derivative, which is a compound represented by a general formula I and a pharmaceutically acceptable salt or hydrate thereof, and wherein R1 and R3

An access to (Z)-ethylenic pseudodipeptides based on ring-closing metathesis

A new access to enantiopure (Z)-ethylenic pseudopeptides, starting from the chiral pool of amino acids and enantiopure 2-substituted-but-3-enoic acids is proposed and illustrated by the syntheses of the (Z)-ethylenic pseudopeptidic analogs of L-Phe-L-Phe, L-Phe-D-Phe, L-Phe-L-Val, L-Phe-D-Val and racemic (LL,DD) and (LD,DL) (phenyl)Gly-Phe. The key-steps of these syntheses are a ring-closing metathesis, catalysed by Grubbs' ruthenium alkykidene complexes, on diethylenic amides and the hydrolytic cleavage of the resulting dihydropyridones under mild conditions through intermediate formation of cyclic imidates.

Enantioconservative synthesis and ring closing metathesis of disubstituted dialkenic amides

Optically pure disubstituted dialkenic amides 2, which are direct precursors of Z-ethylenic pseudo-peptides 1, are readily synthesized and then cyclized to lactams 3 in the presence of Grubbs' ruthenium-based metathesis catalysts with total conservation of enantiomeric purity.

Reaction of N-trityl amino acids with BOP: Efficient synthesis of t-butyl esters as well as N-trityl serine- and threonine-β-lactones

Upon exposure to methoxymethylamine and BOP, the stable hydroxybenzotriazolyl amide of TrPheOH was isolated instead of the expected Weinreb amide. This amide behaves as an active amide similar to the Weinreb amide and could be used, among others, for the

Synthesis of alkene dipeptide isosteres employing the Wittig-Still rearrangement

A new approach to the synthesis of alkene dipeptide isosteres is reported which features the use of the [2,3]-Wittig-Still rearrangement, carried out in hexanes. Employing this rearrangement alkene dipeptide isosteres of 'Gly-Xxx' are accessible starting

New inhibitors of renin that contain novel phosphostatine Leu-Val replacements

A novel series of renin inhibitors based on the Phe8-His9-Leu10-Val11 substructure of renin's natural substrate, angiotensinogen, is reported. These inhibitors retain the Phe8-His9 portion of the native substructure and employ novel phosphostatine Leu10-Val11 replacements (LVRs). The phosphostatine LVRs were prepared by condensing a dialkyl phosphonate ester stabilized anion with either N-t-Boc-amino aldehydes or N-tritylamino aldehydes (derived from the corresponding amino acid). Structure-activity relationships at the Leu10 side chain revealed that the LVR derived from L-cyclohexylalanine provided a 130-fold boost in potency over the LVR derived from L-leucine. The dialkyl ester moiety was varied and a loss in potency was incurred when the alkyl ester was chain extended or α-branced; dimethyl esters provided optimum potency. The phosphonate moiety was replaced by a half-acid half-ester phosphonate and dimethylphosphinate; both replacements lead to a loss in potency. The more potent inhibitors (IC50 = 20-50 nM) were found to be selective inhibitors for renin over porcine pepsin and bovine cathepsin D (little or no inhibition was observed at 10-5 M).

Preparation of Tritylamino Alcohols

N-Tritylamino acid trimethylsilyl esters 2 were mildly reduced with LiAlH4 to give N-tritylamino alcohols 3 in high yields and purity.Other methods provided 3 in lower yields.