96452-48-1

Basic information

• Product Name: benzyl pyridin-2-yl carbonate
• Synonyms: benzyl pyridin-2-yl carbonate
• CAS NO: 96452-48-1
• Molecular Weight: 229.235
• Mol File: 96452-48-1.mol

Chemical Properties

• CAS DataBase Reference: benzyl pyridin-2-yl carbonate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl pyridin-2-yl carbonate(96452-48-1)
• EPA Substance Registry System: benzyl pyridin-2-yl carbonate(96452-48-1)

Safety Data

• Hazardous Substances Data: 96452-48-1(Hazardous Substances Data)

Upstream product

• 142-08-5 2-hydroxypyridin 
• 75-44-5 phosgene 
• 100-51-6 benzyl alcohol 
• 147-85-3 L-proline 
• 501-53-1 benzyl chloroformate 
• 142-08-5 2-Pyridone 

Downstream Products

• 1155-62-0 N-benzyloxycarbonyl-L-glutamic acid 
• 22768-02-1 benzyl ethyl carbonate 
• 3742-91-4 N-(benzyloxycarbonyl)piperidine 
• 25070-73-9 benzyl morpholine-4-carboxylate 
• 31166-44-6 phenylmethyl 1-piperazinecarboxylate 
• 14000-67-0 benzyl 4-(2-hydroxyethyl)-1-piperazinecarboxylate 
• 217795-79-4 benzyl 3-methylpiperidine-1-carboxylate 
• 4892-10-8 (S)-2-((R)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-3-phenyl-propionic acid methyl ester 
• 40182-59-0 Cbz-D-Phe-D-Phe-OMe 
• 252573-87-8 Z-Val-D-Phe-OMe 
• 96452-61-8 N-(Benzyloxycarbonyl)-L-phenylalanin-2-pyridylester 
• 69472-89-5 N-(Benzyloxycarbonyl)-L-valin-2-pyridylester 
• 106561-19-7 Z-D-valyl-D-valine methyl ester 
• 4817-95-2 N-(benzyloxycarbonyl)-L-valyl-L-phenylalanine methyl ester 

Relevant articles and documents

New Amino-protective Reagents for t-Butoxycarbonylation and Benzyloxycarbonylation of Amines and Amino Acids

New amino-protective reagents for t-butoxycarbonylation and benzyloxycarbonylation of amines and amino acids have been developed. t-Butyl 2-pyridyl carbonate and t-butyl S-(2-pyridyl) thiocarbonate react cleanly with various amines and amino acids to afford N-Boc amines and N-Boc amino acids in high yields.Benzyl 2-pyridyl carbonate and O-benzyl S-(2-pyridyl) thiocarbonate are also found to be very effective in the benzyloxycarbonylation of amino acids.

Alkali-metal ion catalysis in alkaline ethanolysis of 2-pyridyl benzoate and benzyl 2-pyridyl carbonate: Effect of modification of nonleaving group from benzoyl to benzyloxycarbonyl

A kinetic study is reported on nucleophilic displacement reactions of benzyl 2-pyridyl carbonate 6 with alkalimetal ethoxides, EtOM (M = Li, Na, and K), in anhydrous ethanol at 25.0 ± 0.1 oC. The plots of pseudo-firstorder rate constant kobsd vs. [EtOM] curve upward, a typical phenomenon reported previously for alkaline ethanolysis of esters in which alkali-metal ions behave as a Lewis-acid catalyst. The kobsd value for the reaction of 6 with a fixed EtOK concentration decreases rapidly upon addition of 18-crown-6-ether (18C6), a complexing agent for K+ ion up to [18C6]/[EtOK] = 1.0 and then remains constant thereafter, indicating that the catalytic effect exerted by K+ ion disappears in the presence of excess 18C6. The reactivity of EtOM towards 6 increases in the order EtO- EtOLi EtONa EtOK, which is contrasting to the reactivity order reported for the corresponding reactions of 2-pyridyl benzoate 4, i.e., EtO- EtOK EtONa EtOLi. Besides, 6 is 1.7 and 3.5 times more reactive than 4 towards dissociated EtO- and ion-paired EtOK, respectively. The reactivity difference and the contrasting metal-ion selectivity are discussed in terms of electronic effects and transition-state structures.

2(1H)-Pyridone as Leaving Group in Acylation Reactions - Applications in Peptide Synthesis

Alkyl 2-pyridyl carbonates 3 or mixtures of 3 and the isomeric N-(alkoxycarbonyl)-2-pyridones 3' are useful for the introduction of urethane protective groups into amino acids.The N-protected amino acids 7 - 10 react with 2(1H)-pyridone (1a) using the carbodiimide method to yield 2-pyridyl active esters 11, which easily undergo coupling reactions with amino acid esters 12 with elimination of 1a to give peptides 13 in good yields as well as high optical purities.