(9S,12S,13R)-12-(cyclohexylmethyl)-9--L-phenylalanyl>-13-hydroxy-2-(2-methylpropyl)-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane

Base Information

• Chemical Name: (9S,12S,13R)-12-(cyclohexylmethyl)-9--L-phenylalanyl>-13-hydroxy-2-(2-methylpropyl)-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane
• CAS No.: 137226-85-8
• Molecular Formula: C₃₆H₅₅N₃O₉
• Molecular Weight: 673.847
• Mol file: 137226-85-8.mol

Synonyms:

Chemical Property of (9S,12S,13R)-12-(cyclohexylmethyl)-9--L-phenylalanyl>-13-hydroxy-2-(2-methylpropyl)-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (9S,12S,13R)-12-(cyclohexylmethyl)-9--L-phenylalanyl>-13-hydroxy-2-(2-methylpropyl)-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane

There total 5 articles about (9S,12S,13R)-12-(cyclohexylmethyl)-9--L-phenylalanyl>-13-hydroxy-2-(2-methylpropyl)-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane 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:

(1S,R)-1-(2-methylpropyl)-5-oxo-5-hydroxypentyl (4S,5R)-4-(cyclohexylmethyl)-2,2-dimethyl-3-<(1,1-dimethylethoxy)carbonyl>-5-oxazolidinecarbxylate (143508-58-1,143508-59-2) → (9S,12S,13R)-12-(cyclohexylmethyl)-9--L-phenylalanyl>-13-hydroxy-2-(2-methylpropyl)-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane (137226-85-8,143614-51-1,143614-52-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / 4-(dimethylamino)pyridine (DMAP), 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC) / CH₂Cl₂ / 0 °C

2: trifluoroacetic acid (TFA) / CH₂Cl₂ / Ambient temperature

3: N-methylmorpholine, hydroxybenzotriazole (HOBt), 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC) / tetrahydrofuran / 144 h / Ambient temperature

4: H₂ / 10 percent Pd/C / methanol / 760 Torr

5: hydroxybenzotriazole monohydrate (HOBt), 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC) / CH₂Cl₂ / 0 - 20 °C

With 4-methyl-morpholine; dmap; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm00099a004

Reference yield:

(9S,12S,13R)-12-(cyclohexylmethyl)-13-hydroxy-2-(2-methylpropyl)-9-<<(phenylmethoxy)carbonyl>amino>-6,10,14-trioxo-1,5-dioxa-11-azacyclotetradecane (137226-84-7,143614-81-7,143614-82-8) → (9S,12S,13R)-12-(cyclohexylmethyl)-9--L-phenylalanyl>-13-hydroxy-2-(2-methylpropyl)-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane (137226-85-8,143614-51-1,143614-52-2)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / 10 percent Pd/C / methanol / 760 Torr

2: hydroxybenzotriazole monohydrate (HOBt), 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC) / CH₂Cl₂ / 0 - 20 °C

With hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/jm00099a004

Reference yield:

(4S,5R)-4-Cyclohexylmethyl-2,2-dimethyl-oxazolidine-5-carboxylic acid 1-[3-((S)-2-benzyloxycarbonylamino-2-carboxy-ethoxycarbonyl)-propyl]-3-methyl-butyl ester → (9S,12S,13R)-12-(cyclohexylmethyl)-9--L-phenylalanyl>-13-hydroxy-2-(2-methylpropyl)-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane (137226-85-8,143614-51-1,143614-52-2)

Guidance literature:

Multi-step reaction with 3 steps

1: N-methylmorpholine, hydroxybenzotriazole (HOBt), 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC) / tetrahydrofuran / 144 h / Ambient temperature

2: H₂ / 10 percent Pd/C / methanol / 760 Torr

3: hydroxybenzotriazole monohydrate (HOBt), 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC) / CH₂Cl₂ / 0 - 20 °C

With 4-methyl-morpholine; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm00099a004

upstream raw materials:

N-tert-butoxycarbonyl-L-phenylalanine

(1S,R)-1-(2-methylpropyl)-5-oxo-5-hydroxypentyl (4S,5R)-4-(cyclohexylmethyl)-2,2-dimethyl-3-<(1,1-dimethylethoxy)carbonyl>-5-oxazolidinecarbxylate

(9S,12S,13R)-12-(cyclohexylmethyl)-13-hydroxy-2-(2-methylpropyl)-9-<<(phenylmethoxy)carbonyl>amino>-6,10,14-trioxo-1,5-dioxa-11-azacyclotetradecane

O^ω-<(5S,R)-5-<<<(4S,5R)-4-(cyclohexylmethyl)-3-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-5-oxazolidinyl>carbonyl>oxy>-4-(2-methylpropyl)pentanoyl>-N^α-<(phenylmethoxy)carbonyl>-L-serine, 1,1-dimethylethyl ester