50903-52-1

Upstream product

• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 771-61-9 2,3,4,5,6-pentafluorophenol 
• 96157-57-2 bis(pentafluorophenyl)sulfite 
• 439912-32-0 propargyl pentafluorophenyl carbonate 

Downstream Products

• 287401-31-4 1-oxo-3-phenyl-2-oxa-5-aza-spiro[3.4]octane-5-carboxylic acid tert-butyl ester 
• 1241920-88-6 (4R,5S,1'S)-4-benzyloxy-1-(N-butyloxycarbonylprolyl)-5-methylpyrrolidin-2-one 
• 128302-56-7 C₆₂H₇₄N₁₄O₁₂ 
• 128302-56-7 C₆₂H₇₄N₁₄O₁₂ 
• 121638-08-2 2,8-Bis<(N-carbonyl-Gly-Phe-NMe2)-Pro-D-Ala-NH>epindolidione 
• 128326-89-6 C₆₄H₇₈N₁₄O₁₂ 
• 78058-03-4 Z-pGlu-Pro-Pro-NH₂ 
• 287401-30-3 tert-butyl-1,1-dimethyl-3-oxo-2-oxa-5-azaspiro[3.4]octan-5-carboxylate 
• 15401-08-8 N-tert-butoxycarbonyl-L-prolyl-L-proline 

Relevant academic research and scientific papers

N-Benzyloxymalimide for an easy access to 5-alkyl-3-pyrrolin-2-ones: Asymmetric synthesis of the mixed imide substructure of the potent immunosuppressant microcolin B

O-Benzyl-N-benzyloxymalimide 12 has been synthesized as a useful variant of the chiral building blocks 9. The advantage of the malimide 12 over 9 was demonstrated by mild and high-yielding reductive N-deprotection of N-benzyloxylactams 18a-i to give a series of (4R,5S)-5-alkyl-4-hydroxy- pyrrolidin-2-ones, which are key intermediates for the asymmetric synthesis of pyrrolidines, pyrrolizidines, and indolizidines, as well as β-hydroxy γ-amino acids. Lactam ent-11a has been applied to the synthesis of the mixed imide 25, a key intermediate for the total synthesis of microcolin B, which also demonstrated that lactam ent-11a or 11a can serve as a latent form of the 5-methyl-3-pyrrolin-2-one substructure of majusculamide D 4, deoxymajusculamide D, and the jamaicamides A-C.

Simultaneous protection and activation of amino acids using propargyl pentafluorophenyl carbonate

A very efficient method for the simultaneous protection of the amino group and activation of the carboxyl group of amino acids is reported using propargyl pentafluorophenyl carbonate (PocOPfp). The amino group is protected as a propargyloxycarbonyl (Poc) derivative, and the carboxyl group is activated as a pentafluorophenyl ester. The yields obtained are good to excellent ranging from 60 to 87%.

Synthesis and Conformational Analysis of Epindolidione-Derived Peptide Models for β-Sheet Formation

Synthesis of 2,8-diaminoepindolidione (2,8-diaminodibenzonaphthyridine-6,12(5,11H)-dione) in 19percent yield from p-nitroaniline is reported, as well as further conversion to 2,8-bis(Boc-L-Pro-Xxx)epindolidione (Xxx=Gly, D-Ala) and then to 2,8-bis(OC(Yyy-Zzz-NMe2)-L-Pro-Xxx)epindolidione (Yyy=Gly, L-Ala, D-Ala; Zzz=Gly, L-Phe, D-Phe).The β-turn-forming tendencies of the series 2,8-bis(X-L-Pro-D-Ala)epindolidione, where X=Ac, Boc, and COGlyOEt, are assigned from 1H NMR evidence.

Bis(pentaluorophenyl) sulfite - A new reagent for the synthesis of activated pentafluorophenyl esters of N-protected amino acids

A method was proposed for the preparation of bis(perfluorophenyl) sulfite, an effective new reagent for the synthesis of pentafluorophenyl esters of N-protected amino acids without racemization.

Prevention of Diketopiperazine Formation in Peptide Synthesis by a Simultaneous Deprotection-Coupling Procedure: Entrapment of Reactive Nucleophilic Species by in situ Acylation

Hydrogenolysis of Z-amino acid-D-Pro-OMe dipeptides in the presence of acetic acid results, almost quantitatively, in the formation of diketopiperazines, whereas in the presence of Boc- or 2-(trimethylsilyl)ethoxycarbonyl protected amino acid pentafluorop