[(3S,11S,12S,13S)-13-Cyclohexylmethyl-12-hydroxy-11-((S)-2-methyl-butylcarbamoyl)-2,6-dioxo-1,7-diaza-cyclotridec-3-yl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [(3S,11S,12S,13S)-13-Cyclohexylmethyl-12-hydroxy-11-((S)-2-methyl-butylcarbamoyl)-2,6-dioxo-1,7-diaza-cyclotridec-3-yl]-carbamic acid tert-butyl ester
• CAS No.: 134916-08-8
• Molecular Formula: C₂₉H₅₂N₄O₆
• Molecular Weight: 552.755

Synonyms:

Chemical Property of [(3S,11S,12S,13S)-13-Cyclohexylmethyl-12-hydroxy-11-((S)-2-methyl-butylcarbamoyl)-2,6-dioxo-1,7-diaza-cyclotridec-3-yl]-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(3S,11S,12S,13S)-13-Cyclohexylmethyl-12-hydroxy-11-((S)-2-methyl-butylcarbamoyl)-2,6-dioxo-1,7-diaza-cyclotridec-3-yl]-carbamic acid tert-butyl ester

There total 11 articles about [(3S,11S,12S,13S)-13-Cyclohexylmethyl-12-hydroxy-11-((S)-2-methyl-butylcarbamoyl)-2,6-dioxo-1,7-diaza-cyclotridec-3-yl]-carbamic acid tert-butyl ester 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:

(S)-4-[(1S,2S,3S)-6-Amino-1-cyclohexylmethyl-2-hydroxy-3-((S)-2-methyl-butylcarbamoyl)-hexylcarbamoyl]-4-tert-butoxycarbonylamino-butyric acid → [(3S,11S,12S,13S)-13-Cyclohexylmethyl-12-hydroxy-11-((S)-2-methyl-butylcarbamoyl)-2,6-dioxo-1,7-diaza-cyclotridec-3-yl]-carbamic acid tert-butyl ester (134916-08-8)

Guidance literature:

With diphenylphosphoranyl azide; In N,N-dimethyl-formamide; at 0 - 4 ℃; for 120h; Yield given;

DOI:10.1016/S0040-4039(00)74351-6

Reference yield:

(S)-2-methylbutylamine (34985-37-0) → [(3S,11S,12S,13S)-13-Cyclohexylmethyl-12-hydroxy-11-((S)-2-methyl-butylcarbamoyl)-2,6-dioxo-1,7-diaza-cyclotridec-3-yl]-carbamic acid tert-butyl ester (134916-08-8)

Guidance literature:

Multi-step reaction with 11 steps

1: EDC, HOBT

2: OsO₄, NaIO₄

3: NaBH₄ / methanol

4: Et₃N / CH₂Cl₂ / 0 °C

5: LiN₃ / dimethylformamide

6: 1,3-propanedithiol, Et₃N

7: Et₃N / CH₂Cl₂

8: HCl / methanol

9: Et₃N, EDC, HOBT

10: H₂ / Pd/C / methanol

11: diphenylphosphoryl azide / dimethylformamide / 120 h / 0 - 4 °C

With 1.3-propanedithiol; hydrogenchloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium azide; diphenylphosphoranyl azide; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)74351-6

Reference yield:

(4S,5S)-5-((S)-1-Carboxy-pent-4-enyl)-4-cyclohexylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (148102-24-3) → [(3S,11S,12S,13S)-13-Cyclohexylmethyl-12-hydroxy-11-((S)-2-methyl-butylcarbamoyl)-2,6-dioxo-1,7-diaza-cyclotridec-3-yl]-carbamic acid tert-butyl ester (134916-08-8)

Guidance literature:

Multi-step reaction with 11 steps

1: EDC, HOBT

2: OsO₄, NaIO₄

3: NaBH₄ / methanol

4: Et₃N / CH₂Cl₂ / 0 °C

5: LiN₃ / dimethylformamide

6: 1,3-propanedithiol, Et₃N

7: Et₃N / CH₂Cl₂

8: HCl / methanol

9: Et₃N, EDC, HOBT

10: H₂ / Pd/C / methanol

11: diphenylphosphoryl azide / dimethylformamide / 120 h / 0 - 4 °C

With 1.3-propanedithiol; hydrogenchloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium azide; diphenylphosphoranyl azide; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)74351-6

upstream raw materials:

(S)-2-methylbutylamine

(4S,5S)-5-((S)-1-Carboxy-pent-4-enyl)-4-cyclohexylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(4S,5S)-4-Cyclohexylmethyl-5-[(S)-4-hydroxy-1-((S)-2-methyl-butylcarbamoyl)-butyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(4S,5S)-4-Cyclohexylmethyl-2,2-dimethyl-5-[(S)-1-((S)-2-methyl-butylcarbamoyl)-pent-4-enyl]-oxazolidine-3-carboxylic acid tert-butyl ester

Downstream raw materials:

{(S)-1-[(3S,11S,12S,13S)-13-Cyclohexylmethyl-12-hydroxy-11-((S)-2-methyl-butylcarbamoyl)-2,6-dioxo-1,7-diaza-cyclotridec-3-ylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

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