344765-03-3

Upstream product

• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 123-11-5 4-methoxy-benzaldehyde 
• 93473-36-0 (S)-2-{[1-(4-Methoxy-phenyl)-meth-(Z)-ylidene]-amino}-3-phenyl-propionic acid methyl ester 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 1010385-00-8 C₁₉H₂₃NO₃ 
• 33402-67-4 sodium hydroxy(4-methoxyphenyl)methanesulfonate 

Downstream Products

• 200559-08-6 (S)-2-[(2-Cyano-acetyl)-(4-methoxy-benzyl)-amino]-3-phenyl-propionic acid methyl ester 
• 344765-12-4 (S)-methyl 2-(2-chloro-N-(4-methoxybenzyl)acetamido)-3-phenylpropanoate 
• 936501-93-8 N-(p-methoxybenzyl)-N-((2S)-chloropropionyl)-L-Phe-OMe 
• 936501-94-9 N-(p-methoxybenzyl)-N-((2R)-chloropropionyl)-L-Phe-OMe 
• 1258512-74-1 (S)-methyl 2-(bromo-N-(4-methoxybenzyl)acetamido)-3-phenylpropanoate 
• 91247-21-1 N-(4-methoxybenzyl)propionamide 
• 916850-87-8 (3S,8aS)-3-benzyl-2-(4-methoxybenzyl)octahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 344765-25-9 4-benzyl-1-(4-methoxy)benzyl-4-methoxycarbonyl-2-azetidinone 
• 344765-44-2 4-benzyl-4-methoxycarbonyl-2-azetidinone 
• 610314-47-1 (R)-2-Benzyl-1-(4-methoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid methyl ester 
• 610314-28-8 (S)-2-Benzyl-1-(4-methoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid methyl ester 
• 936502-19-1 (3S,4S)-4-benzyl-4-carboxy-1-(4-methoxybenzyl)-3-methyl-2-azetidinone 
• 936502-06-6 (3R,4R)-4-benzyl-1-(p-methoxybenzyl)-4-methoxycarbonyl-3-methyl-2-azetidinone 

Relevant academic research and scientific papers

Highly efficient enantioselective synthesis of 1,3-disubstituted 2,5-diketopiperazine derivatives via microwave irradiation

Chiral 2,5-diketopiperazine (2,5-DKP) derivatives have a broad range of biological activities in the medicinal field. The synthetic protocols of 1,3-disubstituted 2,5-DKPs via base-catalyzed cyclization of chloroacetamide have been reported. However, there are several drawbacks, such as an overly long reaction time, low to moderate yield, and racemization of the products. The sequence modified herein of 1,3-disubstituted 2,5-DKPs involves microwave-assisted cyclization. It increases yields and reduces reaction time. Furthermore, employing N-PMB protection prevents racemization, which frequently occurs in the base-catalyzed cyclization reaction. Consequently, the rapid synthetic method of enantiomerically pure 1,3-disubstituted 2,5-DKPs via microwave reaction was established successfully.

Direct reductive alkylation of amine hydrochlorides with aldehyde bisulfite adducts

A mild procedure for the direct reaction of aromatic and aliphatic aldehyde bisulfite adducts with primary and secondary amine hydrochlorides in the presence of sodium cyanoborohydride in methanol is reported.

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.

Selective C-N bond oxidation: demethylation of N-methyl group in N-arylmethyl-N-methyl-α-amino esters utilizing N-iodosuccinimide (NIS)

Demethylation of N-methyl group in N-methyl-N-arylmethyl-α-amino esters was accomplished by the oxidation of the amino group using the N-iodosuccinimide (NIS)/acetonitrile system followed by treatment with O-methylhydroxylamine hydrochloride. This combina

Dynamic diastereoselectivity during iron carbonyl mediated spirocyclization reactions

Dynamic diastereoselectivity during Fe(CO)3 promoted [6 + 2] ene spirocyclization of 35a and 35b, having a chiral center on the pendent side chain, was investigated and gave rise to products 28a and 28b instead of four possible isomers. From th

β-Lactams derived from phenylalanine and homologues: effects of the distance between the aromatic rings and the α-stereogenic reactive center on the memory of chirality

The enantioselectivity in the base-promoted cyclization of N-chloroacetyl derivatives of Phe, Phg, and Hph is dependent on the side-chain length, with the best results for Phg analogues (up to 74% ee). In contrast, shortening of the N-substituent, from a

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.