L-Cysteine,N-[(1,1-dimethylethoxy)carbonyl]-L-cysteinylglycyl-L-prolylglycyl-L-prolyl-,diphenylmethyl ester, cyclic (1®6)-disulfide (9CI)

Base Information

• Chemical Name: L-Cysteine,N-[(1,1-dimethylethoxy)carbonyl]-L-cysteinylglycyl-L-prolylglycyl-L-prolyl-,diphenylmethyl ester, cyclic (1®6)-disulfide (9CI)
• CAS No.: 118002-46-3
• Molecular Formula: C38H48 N6 O9 S2
• Molecular Weight: 796.966
• Mol file: 118002-46-3.mol

Synonyms:Dipyrrolo[2,1-g:2',1'-m][1,2,5,8,11,14,17]dithiapentaazacycloeicosine,cyclic peptide deriv.; Phenceptin

Chemical Property of L-Cysteine,N-[(1,1-dimethylethoxy)carbonyl]-L-cysteinylglycyl-L-prolylglycyl-L-prolyl-,diphenylmethyl ester, cyclic (1®6)-disulfide (9CI)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-Cysteine,N-[(1,1-dimethylethoxy)carbonyl]-L-cysteinylglycyl-L-prolylglycyl-L-prolyl-,diphenylmethyl ester, cyclic (1®6)-disulfide (9CI)

There total 15 articles about L-Cysteine,N-[(1,1-dimethylethoxy)carbonyl]-L-cysteinylglycyl-L-prolylglycyl-L-prolyl-,diphenylmethyl ester, cyclic (1®6)-disulfide (9CI) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 65.0%

N-Boc-S-trityl-L-cysteinyl-glycyl-L-prolyl-glycyl-L-prolyl-S-trityl-L-cysteine benzhydryl ester (118039-05-7) → phenceptin (118002-46-3)

Guidance literature:

With iodine; In pyridine; methanol; dichloromethane; for 2h;

DOI:10.1139/v88-425

Reference yield:

benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride (16652-71-4) → phenceptin (118002-46-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) EEDQ; 2.) triethylamine / 1.) EEDQ, methylene chloride, 5 min; 2.) triethylamine, methylene chloride, RT, 20 h

2: 98 percent / H₂ / 10percent Pd on carbon / methanol / 4 h / atmospheric pressure

3: 1.) EEDQ; 2.) triethylamine / 1.) EEDQ, methylene chloride, RT, 5 min; 2.) triethylamine, RT, 20 h

4: 93 percent / H₂ / 10percent Pd on carbon / methanol / 5 h / atmospheric pressure

5: 1.) EEDQ; 2.) triethylamine / 1.) EEDQ, methanol, 5 min; 2.) triethylamine, 44 h

6: 77 percent / formic acid / 0.42 h / 10 °C

7: 1.) 10 percent citric acid; 2.) EEDQ / 1.) ethyl acetate, 10 percent citric acid; 2.) ethyl acetate, EEDQ, 10 min; 3.) ethyl acetate, 20 h

8: 65 percent / I₂ / methanol; CH₂Cl₂; pyridine / 2 h

With formic acid; hydrogen; iodine; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; citric acid; palladium on activated charcoal; In pyridine; methanol; dichloromethane;

DOI:10.1139/v88-425

Reference yield:

(S)-1-(2-tert-butoxycarbonylaminoacetyl)pyrrolidine-2-carboxylic acid benzyl ester (29776-78-1) → phenceptin (118002-46-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 98 percent / H₂ / 10percent Pd on carbon / methanol / 4 h / atmospheric pressure

2: 1.) EEDQ; 2.) triethylamine / 1.) EEDQ, methylene chloride, RT, 5 min; 2.) triethylamine, RT, 20 h

3: 93 percent / H₂ / 10percent Pd on carbon / methanol / 5 h / atmospheric pressure

4: 1.) EEDQ; 2.) triethylamine / 1.) EEDQ, methanol, 5 min; 2.) triethylamine, 44 h

5: 77 percent / formic acid / 0.42 h / 10 °C

6: 1.) 10 percent citric acid; 2.) EEDQ / 1.) ethyl acetate, 10 percent citric acid; 2.) ethyl acetate, EEDQ, 10 min; 3.) ethyl acetate, 20 h

7: 65 percent / I₂ / methanol; CH₂Cl₂; pyridine / 2 h

With formic acid; hydrogen; iodine; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; citric acid; palladium on activated charcoal; In pyridine; methanol; dichloromethane;

DOI:10.1139/v88-425

upstream raw materials:

N-Boc-S-trityl-L-cysteinyl-glycyl-L-prolyl-glycyl-L-prolyl-S-trityl-L-cysteine benzhydryl ester

benzophenone

benzophenone hydrazone

benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride

Refernces