(S)-4-[(1S,2S,3S)-6-Benzyloxycarbonylamino-1-cyclohexylmethyl-2-hydroxy-3-((S)-2-methyl-butylcarbamoyl)-hexylcarbamoyl]-4-tert-butoxycarbonylamino-butyric acid benzyl ester

Base Information

• Chemical Name: (S)-4-[(1S,2S,3S)-6-Benzyloxycarbonylamino-1-cyclohexylmethyl-2-hydroxy-3-((S)-2-methyl-butylcarbamoyl)-hexylcarbamoyl]-4-tert-butoxycarbonylamino-butyric acid benzyl ester
• CAS No.: 134916-06-6
• Molecular Formula: C₄₄H₆₆N₄O₉
• Molecular Weight: 795.029

Synonyms:

Chemical Property of (S)-4-[(1S,2S,3S)-6-Benzyloxycarbonylamino-1-cyclohexylmethyl-2-hydroxy-3-((S)-2-methyl-butylcarbamoyl)-hexylcarbamoyl]-4-tert-butoxycarbonylamino-butyric acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (S)-4-[(1S,2S,3S)-6-Benzyloxycarbonylamino-1-cyclohexylmethyl-2-hydroxy-3-((S)-2-methyl-butylcarbamoyl)-hexylcarbamoyl]-4-tert-butoxycarbonylamino-butyric acid benzyl ester

There total 11 articles about (S)-4-[(1S,2S,3S)-6-Benzyloxycarbonylamino-1-cyclohexylmethyl-2-hydroxy-3-((S)-2-methyl-butylcarbamoyl)-hexylcarbamoyl]-4-tert-butoxycarbonylamino-butyric acid benzyl 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)-2-methylbutylamine (34985-37-0) → (S)-4-[(1S,2S,3S)-6-Benzyloxycarbonylamino-1-cyclohexylmethyl-2-hydroxy-3-((S)-2-methyl-butylcarbamoyl)-hexylcarbamoyl]-4-tert-butoxycarbonylamino-butyric acid benzyl ester (134916-06-6)

Guidance literature:

Multi-step reaction with 9 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

With 1.3-propanedithiol; hydrogenchloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium azide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; 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) → (S)-4-[(1S,2S,3S)-6-Benzyloxycarbonylamino-1-cyclohexylmethyl-2-hydroxy-3-((S)-2-methyl-butylcarbamoyl)-hexylcarbamoyl]-4-tert-butoxycarbonylamino-butyric acid benzyl ester (134916-06-6)

Guidance literature:

Multi-step reaction with 9 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

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

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

Reference yield:

(4S,5S)-5-[(S)-4-Amino-1-((S)-2-methyl-butylcarbamoyl)-butyl]-4-cyclohexylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester → (S)-4-[(1S,2S,3S)-6-Benzyloxycarbonylamino-1-cyclohexylmethyl-2-hydroxy-3-((S)-2-methyl-butylcarbamoyl)-hexylcarbamoyl]-4-tert-butoxycarbonylamino-butyric acid benzyl ester (134916-06-6)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / CH₂Cl₂

2: HCl / methanol

3: Et₃N, EDC, HOBT

With hydrogenchloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In methanol; dichloromethane;

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

upstream raw materials:

Boc-Glu(OBzl)-OH

(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

Downstream raw materials:

[(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

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