73270-67-4

Upstream product

• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 106-95-6 allyl bromide 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 203873-70-5 (S)-methyl 2-(N-allyl-2-nitrophenylsulfonamido)-3-phenylpropanoate 
• 203873-68-1 (S)-methyl 2-(N-allyl-4-nitrophenylsulfonamido)-3-phenylpropanoate 
• 203873-67-0 (S)-methyl 2-(2-nitrophenylsulfonamido)-3-phenylpropanoate 
• 191337-25-4 (S)-methyl 2-(4-nitrophenylsulphonamido)-3-phenylpropanoate 

Downstream Products

• 203873-71-6 N-allyl-tert-butyloxycarbonyl-L-phenylalaninyl-L-phenylalanine methyl ester 
• 345898-58-0 C₁₅H₁₉ClNO₃P 
• 175207-89-3 (S)-2-(allyl-tert-butoxycarbonylamino)-3-phenylpropionic acid methyl ester 
• 384824-11-7 PHO(CHCH₂NCHC₇H₇CO₂CH₃)2C₂H₄ 
• 861632-48-6 N-(2-propenyl)-N-[[[[N'-(2-propenyl)-N'-(1S)-1-methoxycarbonyl-2-phenyl-ethyl]carbonyl]amino]sulfonyl]-(S)-phenylalanine methyl ester 
• 861632-15-7 N-[[[(2-propenyloxy)carbonyl]amino]sulfonyl]-N-(2-propenyl)-(S)-phenylalanine methyl ester 
• 869560-29-2 (S)-2-(Allyl-benzoyl-amino)-3-phenyl-propionic acid methyl ester 
• 79638-37-2 Boc-(Nall)Phe-OH 
• 292849-74-2 Boc-(Nall)Phe-(Nall)Gly-OEt 
• 1219818-10-6 Boc-Lys(Z)-N(allyl)-Phe-OMe 
• 1632323-19-3 C₁₆H₁₉NO₃ 
• 1632322-90-7 (S)-methyl 2-(4-(4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)-2-oxopyrrolidin-1-yl)-3-phenylpropanoate 
• 1632322-89-4 methyl 2-(4-(4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)-2-oxopyrrolidin-1-yl)-3-phenylpropanoate 
• 1632322-82-7 methyl (S)-2-(2-oxo-2,5-dihydro-1H-pyrrol-1-yl)-3-phenylpropanoate 

Relevant academic research and scientific papers

OLIGOOXOPIPERAZINES AND METHODS OF MAKING AND USING THEM

The present invention relates to oligooxopiperazines and their use. Methods for preparing oligooxopiperazines are also disclosed.

I2-mediated diversity oriented diastereoselective synthesis of amino acid derived trans-2,5-disubstituted morpholines, piperazines, and thiomorpholines

Diastereoselective trans-2,5-disubstituted amino acids derived diverse morpholines, piperazines and thiomorpholines were prepared in 30 min-1 h with high yields through iodine-mediated 6-exotrig type cyclization from a single common synthetic intermediate. The displacement of iodine with hydride ion gave a methyl substituent at the 2-position of morpholines which provides an additional opportunity for diversity oriented nucleophilic substitution on the rings as well as incorporation of substituents at the 5-position from amino acids constituents.

Oligooxopiperazines as nonpeptidic α-helix mimetics

Chemical Reaction Repretatio A new class of nonpeptidic α-helix mlmetics derived from a-amino acids and featuring chlral backbones is described. NMR and circular dichroism spectroscopies, in combination with molecular modeling studies, provide compelling evidence that ollgooxopiperazlne dimers adopt stable conformations that reproduce the arrangement of i, i+4, and i+7 residues on an α-helix.

Synthesis of enantiomerically pure (+)- and (-)-protected 5-aminomethyl-1,3-oxazolidin-2-one derivatives from allylamine and carbon dioxide

The stereoselective synthesis of enantiomerically pure (5R)- and (5S)-aminomethyl-oxazolidinones with different protecting groups have been carried out from an allyl amine as the source of the carbon backbone. The key reaction is the high yield iodiocyclization of enantiomerically pure allylphenethyl amine in the presence of carbon dioxide.

Microwave-accelerated cross-metathesis reactions of N-allyl amino acid substrates

Microwave heating has been utilised for the cross-metathesis reaction of N-allyl amino acid substrates to generate olefin homodimers. Remarkable acceleration of the cross-metathesis reaction (minutes compared to hours) over conventional reflux heating was

LiOH-mediated N-monoalkylation of α-amino acid esters and a dipeptide ester using activated alkyl bromides

Selective N-monoalkylation of α-amino esters with activated alkyl bromides was studied using various alkali or alkali earth metal bases. In the production of N-monoalkylated amino ester derivatives and suppression of N,N-dialkylation, lithium hydroxide wa

N-monoalkylation of α-amino acid esters under solid-liquid PTC conditions

N-(2-Nitrophenylsulfonyl)- (o-NBS-AA-OMe, 4) and N-(4- Nitrophenylsulfonyl)-α-amino acid methyl esters (p-NBSAA-OMe, 5) were N- alkylated with a variety of alkyl halides 6 under solid-liquid phase-transfer catalysis (SL-PTC) conditions, affording the alkylated products o-NBS-N-R2- AA-OMe 7 and p-NBS-N-R2-AA-OMe 8 in excellent yields without any detectable racemization.

Synthesis of cyclic dipeptides by ring-closing metathesis

Several cyclic dipeptides (4a-g and 9a-c) have been synthesized by 'amide-to-amide' cyclization of 2a-g and 8a-c, respectively, by means of ring-closing metathesis employing the Grubbs ruthenium catalyst. The influence of additives as well as the length of the amide substituent were studied. Best yields were obtained by cyclization in solution with either lithium fluoroacetate or α,α-dichlorotoluene as an additive.

Conformationally constrained substance P analogues: The total synthesis of a constrained peptidomimetic for the Phe7-Phe8 region

A lactam-based peptidomimetic for the Phe7-Phe8 region of substance P has been synthesized. The synthesis used an anodic amide oxidation to selectively functionalize the C5-position of a 3-pheylproline derivative. The resulting proline derivative was coupled to a Cbz-protected phenylalanine, and an intramolecular reductive amination strategy used to convert the coupled material into a bicyclic piperazinone ring skeleton. The net result was a dipeptide building block that imbedded one of two proposed receptor bound conformations for the Phe7-Phe8 region of substance P into a bicyclic ring skeleton. The building block was then converted into a constrained substance P analogue with the use of solid-phase peptide synthesis. A similar intramolecular reductive amination strategy was used to synthesize a substance P analogue having only Phe7 constrained, and the original 3-phenylproline was converted into a substance P analogue having only Phe8 constrained. All of the analogues were examined for their ability to displace substance P from its NK-1 receptor.

Site-specific N-alkylation of peptides on the solid phase

A convenient approach, featuring a Mitsunobu reaction, is described for the introduction of an alkyl group at a specific amide function of a peptide on the solid phase. This 'site-specific alkylation' procedure is illustrated with an N-ethyl scan of Leu-enkephalin.