(3S,4aS,8aS)-2-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

Base Information

• Chemical Name: (3S,4aS,8aS)-2-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide
• CAS No.: 150323-20-9
• Molecular Formula: C₄₁H₆₃N₃O₄Si
• Molecular Weight: 690.054

Synonyms:(3S,4aS,8aS)-2-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

Chemical Property of (3S,4aS,8aS)-2-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of (3S,4aS,8aS)-2-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide

There total 8 articles about (3S,4aS,8aS)-2-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide 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:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → (3S,4aS,8aS)-2-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide (150323-20-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 96 percent / imidazole / CH₂Cl₂ / 4 h / 0 - 20 °C

2: 1.) LDA / 1.) THF, hexane, 30 min, 2.) THF, hexane, 3 h

3: 97 percent / 49percent aq. HF / acetonitrile / 18 h / Ambient temperature

4: Et₃N / CH₂Cl₂

5: 35 percent / K₂CO₃ / xylene / 140 °C

6: 1M LiOH / 1,2-dimethoxy-ethane / 3 h / Ambient temperature

7: imidazole / dimethylformamide / Ambient temperature

8: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt / dimethylformamide

With 1H-imidazole; lithium hydroxide; hydrogen fluoride; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium diisopropyl amide; In 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; xylene;

DOI:10.1021/jm00047a001

Reference yield:

(5S)-(5-tert-butyldimethylsilyloxymethyl)furan-2(5H)-one (62396-80-9) → (3S,4aS,8aS)-2-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide (150323-20-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) LDA / 1.) THF, hexane, 30 min, 2.) THF, hexane, 3 h

2: 97 percent / 49percent aq. HF / acetonitrile / 18 h / Ambient temperature

3: Et₃N / CH₂Cl₂

4: 35 percent / K₂CO₃ / xylene / 140 °C

5: 1M LiOH / 1,2-dimethoxy-ethane / 3 h / Ambient temperature

6: imidazole / dimethylformamide / Ambient temperature

7: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt / dimethylformamide

With 1H-imidazole; lithium hydroxide; hydrogen fluoride; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium diisopropyl amide; In 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; xylene;

DOI:10.1021/jm00047a001

Reference yield:

3R,5S-3-Benzyl-5-mesyloxymethyl-4,5-dihydro-2(3H)-furanon (150323-17-4) → (3S,4aS,8aS)-2-[(2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((1S,2R)-2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-decahydro-isoquinoline-3-carboxylic acid tert-butylamide (150323-20-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 35 percent / K₂CO₃ / xylene / 140 °C

2: 1M LiOH / 1,2-dimethoxy-ethane / 3 h / Ambient temperature

3: imidazole / dimethylformamide / Ambient temperature

4: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt / dimethylformamide

With 1H-imidazole; lithium hydroxide; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,2-dimethoxyethane; N,N-dimethyl-formamide; xylene;

DOI:10.1021/jm00047a001

upstream raw materials:

(1S,2R)-1-amino-2-indanol

(2R,4S)-2-Benzyl-5-((3S,4aS,8aS)-3-tert-butylcarbamoyl-octahydro-isoquinolin-2-yl)-4-(tert-butyl-dimethyl-silanyloxy)-pentanoic acid

(5S)-(5-tert-butyldimethylsilyloxymethyl)furan-2(5H)-one

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

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