93473-36-0

Upstream product

• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 2566-35-0 N-methylphenylalanine 
• 1415421-62-3 (1R,3R)-methyl 1-benzyl-4,9-dihydroxy-3-(4-methoxyphenyl)-2,3-dihydro-1Hbenzo[f]isoindole-1-carboxylate 
• 344765-03-3 2-(4-methoxybenzylamino)-3-phenypropionic acid methyl ester 
• 1610827-77-4 C₃₃H₄₃NO₆ 
• 1610827-60-5 C₃₃H₄₃NO₆ 
• 1610827-61-6 C₃₃H₄₃NO₆ 
• 91247-21-1 N-(4-methoxybenzyl)propionamide 
• 104739-62-0 N-(2-Boc-amino-3-methylbutyliden)-L-phenylalanin-N-oxid-methylester 
• 104739-58-4 N-(2-Boc-aminopropyliden)-L-phenylalanin-N-oxid-methylester 
• 104739-66-4 N-(2-Boc-amino-3-phenylpropyliden)-L-phenylalanin-N-oxid-methylester 
• 53933-45-2 (S)-1-Methoxycarbonyl-2-phenylethylhydroxylamine 
• 344765-12-4 (S)-methyl 2-(2-chloro-N-(4-methoxybenzyl)acetamido)-3-phenylpropanoate 
• 344765-25-9 4-benzyl-1-(4-methoxy)benzyl-4-methoxycarbonyl-2-azetidinone 
• 344765-44-2 4-benzyl-4-methoxycarbonyl-2-azetidinone 

Relevant academic research and scientific papers

Stereospecific synthesis of pyrrolidines with varied configurations via 1,3-dipolar cycloadditions to sugar-derived enones

Enantiomerically pure pyrrolidines have been obtained by 1,3-dipolar cycloaddition of stabilized azomethine ylides and sugar enones (dihydropyranones) derived from pentoses. Thus, the S-enone (menthyl 3,4-dideoxy-(1S)-pent-3-enopyranosid-2-ulose) was prepared from d-xylose, while the R analogue was obtained from l-arabinose. The dipoles were generated in situ from α-arylimino esters of common amino acids (glycine, alanine, or phenylalanine) and aromatic aldehydes (benzaldehyde, 3-formylpyridine and 4-methoxybenzaldehyde). Under optimized conditions, the cycloaddition reactions were highly diastereo- and regioselective to yield, in most of the cases, a very major adduct of the 16 theoretically possible. The diastereoselectivity relies on the strict stereocontrol exerted by the stereogenic center of the pyranone. Thus, the (S)-enone, derived from d-xylose, gave tetrasubstituted pyrrolidines having a defined stereochemistry for the four stereocenters of the ring, while they had the opposite configuration when starting from the (R)-dihydropyranone. Furthermore, some endo-cycloadducts underwent isomerization of the carbons vicinal to the nitrogen atom to afford pyrrolidines with a rather unusual stereochemistry for the direct dipolar cycloadditions.

Mild construction of 3-methyl tetramic acids enabling a formal synthesis of palau'imide

A general method to construct 3-methyl-4-O-methylated tetramic acids displaying a C-5 stereocenter is presented. The synthetic sequence employs a SmI2-mediated cyclization, whereby the chirality of the emerging tetramic acid core is retained from the starting chiral amino acid. Application to palau'imide is discussed.

Efficient solid-phase synthesis of highly functionalized 1,4-benzodiazepin-5-one derivatives and related compounds by intramolecular aza-wittig reactions

Due to their widespread biological activities and favorable pharmacokinetic properties, benzodiazepines were among the first classes of small molecules to be synthesized on solid supports. Since then, there have been numerous reports on the synthesis of similar skeletons. We have employed the T1 triazene linker to yield 1,4-benzodiazepin-5-one. Starting from various substituted triazene resins, cleavage in the presence of an azide donor, such as trimethylsilylazide, gave rise to aryl azides. Intramolecular aza-Wittig reactions produced the appropriately functionalized N-heterocycles. By using this route, the natural product deoxyvasicinone and related compounds were prepared.

Amino acid-derived 4-alkyl-4-carboxy-2-azetidinones. New insights into β-lactam ring formation and n-deprotection

The preparation and N-deprotection of a series of phenylalanine-derived 2-azetidinones incorporating 2,4-dimethoxybenzyl (Dmb), 2,3,4-, 2,4,6- and 3,4,5-trimethoxybenzyl (Tmb) groups at 1 position are described. The base-promoted cyclization of the corresponding methoxy-substituted Nαbenzyl-Nα-chloroacetyl derivatives to the 1,4,4-trisubstituted azetidinones proceeded with moderate to good yields, except for the 2,4,6-Tmb analogue. In spite of the number and position of the OMe groups, N-unsubstituted β-lactams were obtained by oxidative debenzylation using potassium peroxodisulfate. Alternatively, debenzylation of Pmb, Dmb and Tmb 2-azetidinones with TFA/anisole resulted in concomitant β-lactam opening to α-benzylaspartic acid derivatives.

X=Y-ZH Systems as Potential 1,3-Dipoles. Part 8. Pyrrolidines and Δ5-Pyrrolines (3,7-Diazabicyclooctenes) from the Reaction of Imines of α-Amino Acids and their Esters with Cyclic Dipolarophiles. Mechanism of Racemisation of α-Amino Acid

Imines of α-amino acid esters with aromatic, heterocyclic, and aliphatic aldehydes generate azomethine ylides stereospecifically by a prototropic shift on heating in toluene.The azomethine ylides undergo cycloaddition to N-phenylmaleimide, maleic anhydrid

"Nitrono" Peptides, I. - An Isomeric and Isoelectronic Equivalent of the Peptide Bond

Optically active Boc-α-L-amino aldehydes 1 are converted with N-hydroxy-α-L-amino acid methyl esters 2 into the N-blocked "nitrono" dipeptide esters 3a-l.