113304-79-3

Upstream product

• 75-44-5 phosgene 
• 2592-95-2 benzotriazol-1-ol 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 104-54-1 3-Phenylpropenol 
• 80029-43-2 1-hydroxybenzotriazol-hydrate 

Downstream Products

• 97988-96-0 (S)-2-((E)-3-Phenyl-allyloxycarbonylamino)-propionic acid 
• 97989-07-6 (2S,3R)-3-Hydroxy-2-((E)-3-phenyl-allyloxycarbonylamino)-butyric acid 
• 97988-98-2 (S)-2-((E)-3-Phenyl-allyloxycarbonylamino)-succinic acid 
• 97989-13-4 Coc-Leu-Gly-OEt 
• 97988-97-1 3-((E)-3-Phenyl-allyloxycarbonylamino)-propionic acid 
• 113350-96-2 (S)-Pyrrolidine-1,2-dicarboxylic acid 1-((E)-3-phenyl-allyl) ester 
• 25084-56-4 Coc-Gly-OEt 
• 3742-89-0 N-cinnamyloxycarbonylglycine 
• 97989-04-3 (S)-3-Phenyl-2-((E)-3-phenyl-allyloxycarbonylamino)-propionic acid 
• 97989-03-2 (S)-4-Methylsulfanyl-2-((E)-3-phenyl-allyloxycarbonylamino)-butyric acid 
• 97989-02-1 (2S,3S)-3-Methyl-2-((E)-3-phenyl-allyloxycarbonylamino)-pentanoic acid 
• 97989-01-0 (S)-4-Methyl-2-((E)-3-phenyl-allyloxycarbonylamino)-pentanoic acid 
• 97989-06-5 (S)-3-Hydroxy-2-((E)-3-phenyl-allyloxycarbonylamino)-propionic acid 
• 97989-08-7 (S)-3-Methyl-2-((E)-3-phenyl-allyloxycarbonylamino)-butyric acid 

Relevant academic research and scientific papers

APPLICATION OF CINNAMYLOXYCARBONYL (Coc) PROTECTION DURING THE SYNTHESIS OF Coc-Pro-MePhe-MeAla-OMe. CHAIN RUPTURE OF THE TRIPEPTIDE ON CHROMATOGRAPHY.

The preparation of 1-(cinnamyloxycarbonyloxy)benztriazole (Coc-OBt), as reported in literature, results in a mixture of 50percent Coc-OBt (6) next to 13percent of 1-(cinnamyloxy)benztriazole (7).The reagent 6 is stable for several months in the fridge.Coc-protection of Pro can be obtained in an improved yield by a slightly modified procedure.Coc-Pro-MePhe-MeAla-OMe was prepared in good yields using BOP-Cl as the activator for coupling.In an attempt to isolate the tripeptide by chromatography on SiO2 we found it to decompose into Coc-Pro and the cyclic dipeptide (DKP) c(MePhe-MeAla).The same DKP is formed from the dipeptide ester salt Tfa.MePhe-MeAla-OMe on standing in CDCl3.These findings stress the ease of chain rupture of peptides caused by acidic agents when they possess a triad of N-alkylated amino acids (3).

THE CINNAMYLOXYCARBONYL GROUP AS A NEW AMINO-PROTECTING GROUP

A new urethane-type protecting group for amines, cinnamyloxycarbonyl (Coc) group, is described.The cleavage of the Coc group is effectively catalyzed by 5 molpercent of in the presence of formic acid, pyridine, and N-hydroxysuccinimide in ref