112700-41-1

Upstream product

• 109579-08-0 (S)-[1-benzyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 
• 4530-18-1 N-(tert-butoxycarbonyl)-L-phenylalanine 
• 142955-51-9 N-butoxycarbonyl-L-phenylalanine anhydride 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 112700-36-4 (2'S)-5-<(1-hydroxy-3-phenyl-2-t-butoxycarbonylamino)-propylidene>-2,2-dimethyl-1,3-dioxane-4,6-dione 

Downstream Products

• 612484-64-7 (3E,5S)-5-benzyl-1-(tert-butoxycarbonyl)-3-[(dimethylamino)methylidene]pyrrolidine-2,4-dione 
• 109579-10-4 (4S,5S)-5-Benzyl-1-(tert-butyloxycarbonyl)-4-hydroxypyrrolidin-2-one 
• 1282523-13-0 (2'S,5S)-2',5-dibenzyl-4-hydroxy-1H,1'H-[3,3'-bipyrrole]-2,5'(2'H,5H)-dione 
• 128892-65-9 (S)-5-Benzyl-4-hydroxy-1,5-dihydro-pyrrol-2-one 
• 123884-01-5 (5S)-benzyl-4-methoxy-2,5-dihydropyrrol-2-one 

Relevant academic research and scientific papers

Total synthesis of modified pentapeptide, caldoramide

Total synthesis of modified pentapeptide, caldoramide, a cytotoxic linear pentapeptide from the marine cyanobacterium Caldora penicillate is described. Notable features of the route include the efficient preparation of three key fragments and final assemb

Expanding the scope of oligo-pyrrolinone-pyrrolidines as protein-protein interface mimics

Oligo-pyrrolinone-pyrrolidines (generic structure 1) have the potential to interfere with protein-protein interactions (PPIs), but to reduce this to practice it is necessary to be able to synthesize these structures with a variety of different side chains

Cytotoxic tetramic acid derivative produced by a plant type-III polyketide synthase

The tetramic acid (2,4-pyrrolidinedione) scaffold has been recognized as an important structural feature because of its mycotoxic, antibacterial, antiviral, and antioxidant activities. This important class of natural products is reportedly produced by the type-I polyketide synthase/nonribosomal peptide synthetase (PKS/NRPS) hybrid megaenzyme systems. In contrast, the benzalacetone synthase (BAS) from Rheum palmatum is a structurally simple, plant-specific type-III PKS that catalyzes the one-step decarboxylative condensation of malonyl-CoA with 4-coumaroyl-CoA. The type-III PKS exhibits unusually broad substrate specificity and notable catalytic versatility. Here we report that R. palmatum BAS efficiently produces a series of unnatural, novel tetramic acid derivatives by the condensation of malonyl-CoA with aminoacyl-CoA thioesters chemically synthesized from l- and d-amino acids. Remarkably, the novel tetramic acid dimer d-5 formed from d-phenylalanoyl-CoA showed moderate antiproliferative activity against murine leukemia P388 cells.

Synthesis of acylated active methylene compounds with N-boc-L-phenylalanine and their heterocyclization, both achieved enantioselectively

Three active methylene compounds, malononitrile, methyl cyanoacetate and Meldrum's acid, have been found to be acylated effectively with N-Boc-L-phenylalanine using carbonyldiimidazole (CDI) activation conditions. Two of the aminoacetyl derivatives isolat

Synthesis of N-substituted 3-ammomethylidenetetramic acids

(S)-3-(Dimethylamino)methylidene-5-benzyltetramic acid derivatives 4a and 4b were prepared in three steps from N-protected (S)-3-phenylalanines 1a and 1b, respectively. Similarly, N-[N-(benzyloxycarbonyl)glycyl]grycine (1c) was transformed into the enamitione 4c. Acid-catalysed coupling of enaminones 4a-c with aliphatic, aromatic, and heteroaromatic primary amines 5-34 afforded the corresponding N(3′)-substituted 3-aminomethylidenetetramic acid derivatives 35-64 in 29-96% yields. Georg Thieme Verlag Stuttgart.

A facile solid phase synthesis of tetramic acid

The condensation of N-acylated amino acids with polymer-supported cyclic malonic acid ester was carried out in the presence of DCC/DMAP. The cyclisation of the intermediate resin, by heating in an organic solvent, gave the N-protected tetramic acid derivatives in good yields and high purity.

Design of potential new HIV protease inhibitors: Enantioconvergent synthesis of new pyrrolidin-3-ol, and pyrrolidin-3-one peptide conjugates

Novel potential HIV protease inhibitors are obtained by an enantioconvergent synthesis of mimicking Phe-Pro dipeptides, achieved through the coupling between Boc(L)Phe or Boc(L)Tyr and both enantiomers of syn-2-benzylpyrrolidin-3-ol and their correspondin

Synthesis of Chiral Urethane N-Alkoxycarbonyl Tetramic Acids from Urethane N-Carboxyanhydrides (UNCAs)

The synthesis of chiral N-protected tetramic acid derivatives which are precursors of β-hydroxy γ-amino acid under mild conditions is described.Reaction of urethane-N-carboxyanhydrides (UNCAs) with Meldrum's acid in the presence of a tertiary amine, follo

Stereospecific Synthesis of N-Protected Statine and Its Analogues via Chiral Tetramic Acid

The condensation of a chiral N-protected amino acid with Meldrum's acid in the presence of isopropenyl chloroformate (IPCF) and of 4-N,N-dimethylaminopyridine (DMAP) has been examined.The cyclisation of the reaction product, by heating in an organic solve