27544-35-0

Basic information

• Product Name: L-Proline, 1-[N-[(phenylmethoxy)carbonyl]-L-alanyl]-, 1,1-dimethylethyl ester
• CAS NO: 27544-35-0
• Molecular Formula: C20H28N2O5
• Molecular Weight: 376.453
• Mol File: 27544-35-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: L-Proline, 1-[N-[(phenylmethoxy)carbonyl]-L-alanyl]-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Proline, 1-[N-[(phenylmethoxy)carbonyl]-L-alanyl]-, 1,1-dimethylethyl ester(27544-35-0)
• EPA Substance Registry System: L-Proline, 1-[N-[(phenylmethoxy)carbonyl]-L-alanyl]-, 1,1-dimethylethyl ester(27544-35-0)

Safety Data

• Hazardous Substances Data: 27544-35-0(Hazardous Substances Data)

Upstream product

• 2812-46-6 proline tert-butyl ester 
• 501-53-1 benzyl chloroformate 
• 540-88-5 acetic acid tert-butyl ester 
• 1142-20-7 N-Cbz-Ala 
• 541-41-3 chloroformic acid ethyl ester 
• 83283-35-6 Proline tert-butyl ester dibenzenesulfimide salt 
• 16357-59-8 N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline 
• 139375-78-3 (S)-1-{2-[(Z)-Hydroxyimino]-propionyl}-pyrrolidine-2-carboxylic acid tert-butyl ester 

Downstream Products

• 29375-30-2 (S)-alanyl-(S)-proline tert-butyl ester 
• 120791-98-2 N-(Benzyloxycarbonyl)-L-alanyl-L-prolyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonyl-O-tert-butyl-L-seryl-O-tert-butyl-L-seryl-O-tert-butyl-L-serin-tert-butylester 
• 120792-21-4 C₅₆H₆₆N₄O₂₃ 
• 120792-03-2 N-(Benzyloxycarbonyl)-L-alanyl-L-prolyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonyl-O-tert-butyl-L-seryl-O-tert-butyl-L-serin-tert-butylester 
• 120791-84-6 N-(Benzyloxycarbonyl)-L-alanyl-L-prolyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonyl-O-tert-butyl-L-serin-tert-butylester 
• 120791-99-3 L-Alanyl-L-prolyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-seryl-L-seryl-L-serin 
• 120792-04-3 L-Alanyl-L-prolyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-seryl-L-serin 
• 120791-83-5 N-(Benzyloxycarbonyl)-L-alanyl-L-prolyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonin-tert-butylester 
• 120791-86-8 L-Alanyl-L-prolyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-serin 
• 120791-85-7 L-Alanyl-L-prolyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonin 
• 120792-20-3 N-(Benzyloxycarbonyl)-L-alanyl-L-prolyl-O-<(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2-acetamido-4,6-di-O-benzoyl-2-desoxy-α-D-galactopyranosyl)>-L-threonin-tert-butylester 
• 120173-73-1 N-(Benzyloxycarbonyl)-L-alanyl-L-prolyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-L-threonin 
• 120792-27-0 L-Alanyl-L-prolyl-O-(2-acetamido-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-seryl-L-seryl-L-serin 
• 120792-26-9 L-Alanyl-L-prolyl-O-(2-acetamido-2-desoxy-α-D-galactopyranosyl)-L-threonyl-L-seryl-L-serin 

Relevant articles and documents

Allenone-Mediated Racemization/Epimerization-Free Peptide Bond Formation and Its Application in Peptide Synthesis

Allenone has been identified as a highly effective peptide coupling reagent for the first time. The peptide bond was formed with an α-carbonyl vinyl ester as the key intermediate, the formation and subsequent aminolysis of which proceed spontaneously in a racemization-/epimerization-free manner. The allenone coupling reagent not only is effective for the synthesis of simple amides and dipeptides but is also amenable to peptide fragment condensation and solid-phase peptide synthesis (SPPS). The robustness of the allenone-mediated peptide bond formation was showcased incisively by the synthesis of carfilzomib, which involved a rare racemization-/epimerization-free N to C peptide elongation strategy. Furthermore, the successful synthesis of the model difficult peptide ACP (65-74) on a solid support suggested that this method was compatible with SPPS. This method combines the advantages of conventional active esters and coupling reagents, while overcoming the disadvantages of both strategies. Thus, this allenone-mediated peptide bond formation strategy represents a disruptive innovation in peptide synthesis.

Water-removable ynamide coupling reagent for racemization-free syntheses of peptides, amides, and esters

A novel ynamide coupling reagent, the by-product of which can be removed by water, was reported. It promotes the direct coupling between carboxylic acids and amines, alcohols or thiols to provide amides, peptides, esters and thioesters, respectively. No detectable racemization was observed for all the coupling reactions of carboxylic acids containing an α-chiral center. Importantly, a simple acidic aqueous work-up removed the by-product readily to afford pure coupling products in good to excellent yields without the use of column chromatography, thus making this method more environmentally benign, user friendly and cost-effective. The robustness of the water-removable ynamide coupling reagent was further exemplified by the racemization/epimerization-free synthesis of carfilzomib, in which no column chromatography purification was involved for the entire 12-step synthesis.

A Novel Method for Preparation of Optically Active Dipeptide. Chemo- and Stereoselective Reduction of 2-Hydroxyimino Amides with Samarium Diiodide

Various α,β-unsaturated amides derived from α-amino acids are converted to the corresponding 2-hydroxyimino amides of α-amino acids by the reaction with butyl nitrite and silane, which are directly reduced with samarium diiodide to the optically active di