(3R,4S,7S)-4-(cyclohexylmethyl)-7-<<(1,1-dimethylethoxy)carbonyl>amino>-3-hydroxy-2,6,10-trioxo-1-oxa-5,9-diazacyclotetradecane

Base Information

• Chemical Name: (3R,4S,7S)-4-(cyclohexylmethyl)-7-<<(1,1-dimethylethoxy)carbonyl>amino>-3-hydroxy-2,6,10-trioxo-1-oxa-5,9-diazacyclotetradecane
• CAS No.: 134848-95-6
• Molecular Formula: C₂₃H₃₉N₃O₇
• Molecular Weight: 469.579

Synonyms:(3R,4S,7S)-4-(cyclohexylmethyl)-7-<<(1,1-dimethylethoxy)carbonyl>amino>-3-hydroxy-2,6,10-trioxo-1-oxa-5,9-diazacyclotetradecane

Chemical Property of (3R,4S,7S)-4-(cyclohexylmethyl)-7-<<(1,1-dimethylethoxy)carbonyl>amino>-3-hydroxy-2,6,10-trioxo-1-oxa-5,9-diazacyclotetradecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,7S)-4-(cyclohexylmethyl)-7-<<(1,1-dimethylethoxy)carbonyl>amino>-3-hydroxy-2,6,10-trioxo-1-oxa-5,9-diazacyclotetradecane

There total 7 articles about (3R,4S,7S)-4-(cyclohexylmethyl)-7-<<(1,1-dimethylethoxy)carbonyl>amino>-3-hydroxy-2,6,10-trioxo-1-oxa-5,9-diazacyclotetradecane 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:

3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9,26354-94-9) → (3R,4S,7S)-4-(cyclohexylmethyl)-7-<<(1,1-dimethylethoxy)carbonyl>amino>-3-hydroxy-2,6,10-trioxo-1-oxa-5,9-diazacyclotetradecane (134848-95-6)

Guidance literature:

Multi-step reaction with 7 steps

1: NaOH / H₂O / 70 °C

2: Bu₄NBr / acetone / 24 h / Heating

3: 99 percent / 4-(dimethylamino)pyridine (DMAP), 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDC) / CH₂Cl₂ / 0 °C

4: TFA / CH₂Cl₂ / Ambient temperature

5: hydroxybenzotriazole monohydrate (HOBt), 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (ECD) / CH₂Cl₂ / 0 - 20 °C

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

7: diphenyl phosphorazidate (DPPA), Et₃N / dimethylformamide / 1.) 0 deg C, 2.) 7.5 deg C, 3 d, 3.) RT, 16 h

With dmap; sodium hydroxide; diphenyl phosphoryl azide; tetrabutylammomium bromide; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm00113a005

Reference yield:

5-hydroxypentanoic acid sodium salt (37435-69-1) → (3R,4S,7S)-4-(cyclohexylmethyl)-7-<<(1,1-dimethylethoxy)carbonyl>amino>-3-hydroxy-2,6,10-trioxo-1-oxa-5,9-diazacyclotetradecane (134848-95-6)

Guidance literature:

Multi-step reaction with 6 steps

1: Bu₄NBr / acetone / 24 h / Heating

2: 99 percent / 4-(dimethylamino)pyridine (DMAP), 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDC) / CH₂Cl₂ / 0 °C

3: TFA / CH₂Cl₂ / Ambient temperature

4: hydroxybenzotriazole monohydrate (HOBt), 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (ECD) / CH₂Cl₂ / 0 - 20 °C

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

6: diphenyl phosphorazidate (DPPA), Et₃N / dimethylformamide / 1.) 0 deg C, 2.) 7.5 deg C, 3 d, 3.) RT, 16 h

With dmap; diphenyl phosphoryl azide; tetrabutylammomium bromide; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm00113a005

Reference yield:

benzyl 5-hydroxy pentanoate (134848-96-7) → (3R,4S,7S)-4-(cyclohexylmethyl)-7-<<(1,1-dimethylethoxy)carbonyl>amino>-3-hydroxy-2,6,10-trioxo-1-oxa-5,9-diazacyclotetradecane (134848-95-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 99 percent / 4-(dimethylamino)pyridine (DMAP), 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDC) / CH₂Cl₂ / 0 °C

2: TFA / CH₂Cl₂ / Ambient temperature

3: hydroxybenzotriazole monohydrate (HOBt), 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (ECD) / CH₂Cl₂ / 0 - 20 °C

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

5: diphenyl phosphorazidate (DPPA), Et₃N / dimethylformamide / 1.) 0 deg C, 2.) 7.5 deg C, 3 d, 3.) RT, 16 h

With dmap; diphenyl phosphoryl azide; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00113a005

upstream raw materials:

3,4,5,6-tetrahydro-2H-pyran-2-one

5-hydroxypentanoic acid sodium salt

benzyl 5-hydroxy pentanoate

5-oxo-5-(phenylmethoxy)pentyl (4S,5R)-4-(cyclohexylmethyl)-2,2-dimethyl-3-<(1,1-dimethylethoxy)carbonyl>-5-oxazolidinecarboxylate

Downstream raw materials:

(3R,4S,7S)-4-(cyclohexylmethyl)-7-<-L-phenylalanyl>amino>-3-hydroxy-2,6,10-trioxo-1-oxa-5,9-diazacyclotetradecane

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