2(R)-(phenylmethyl)-4(S)-<(tert-butyldimethylsilyl)oxy>-5-<1-<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>>pentanoic acid

Base Information

• Chemical Name: 2(R)-(phenylmethyl)-4(S)-<(tert-butyldimethylsilyl)oxy>-5-<1-<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>>pentanoic acid
• CAS No.: 174139-99-2
• Molecular Formula: C₃₂H₅₅N₃O₆Si
• Molecular Weight: 605.891

Synonyms:2(R)-(phenylmethyl)-4(S)-<(tert-butyldimethylsilyl)oxy>-5-<1-<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>>pentanoic acid

Chemical Property of 2(R)-(phenylmethyl)-4(S)-<(tert-butyldimethylsilyl)oxy>-5-<1-<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>>pentanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2(R)-(phenylmethyl)-4(S)-<(tert-butyldimethylsilyl)oxy>-5-<1-<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>>pentanoic acid

There total 12 articles about 2(R)-(phenylmethyl)-4(S)-<(tert-butyldimethylsilyl)oxy>-5-<1-<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>>pentanoic acid 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) → 2(R)-(phenylmethyl)-4(S)-<(tert-butyldimethylsilyl)oxy>-5-<1-<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>>pentanoic acid (174139-99-2)

Guidance literature:

Multi-step reaction with 7 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: 96 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 0 °C

5: 83 percent / (i-Pr)2NEt / propan-2-ol / 3.5 h

6: aq. LiOH / 1,2-dimethoxy-ethane / 0.5 h

7: imidazole / 1,2-dimethoxy-ethane / 20 h / 0 - 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; lithium hydroxide; hydrogen fluoride; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In 1,2-dimethoxyethane; dichloromethane; isopropyl alcohol; acetonitrile;

DOI:10.1021/jm00047a001

Reference yield:

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) → 2(R)-(phenylmethyl)-4(S)-<(tert-butyldimethylsilyl)oxy>-5-<1-<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>>pentanoic acid (174139-99-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 40percent NaOH / dioxane; H₂O / 2.5 h

2: 40percent NaOH / dioxane; H₂O / 14 h

3: 85 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt, Et₃N / dimethylformamide / 18 h

4: 96 percent / H₂ / 10percent Pd/C / methanol / 3 h

5: 83 percent / (i-Pr)2NEt / propan-2-ol / 3.5 h

6: aq. LiOH / 1,2-dimethoxy-ethane / 0.5 h

7: imidazole / 1,2-dimethoxy-ethane / 20 h / 0 - 20 °C

With 1H-imidazole; lithium hydroxide; sodium hydroxide; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; 1,2-dimethoxyethane; water; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/jm00047a001

Reference yield:

(S)-4-(tert-butoxycarbonyl)piperazine-2-carboxylic acid (848482-93-9) → 2(R)-(phenylmethyl)-4(S)-<(tert-butyldimethylsilyl)oxy>-5-<1-<4-<(1,1-dimethylethoxy)carbonyl>-2(S)-(N-tert-butylcarbamoyl)piperazinyl>>pentanoic acid (174139-99-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 40percent NaOH / dioxane; H₂O / 14 h

2: 85 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt, Et₃N / dimethylformamide / 18 h

3: 96 percent / H₂ / 10percent Pd/C / methanol / 3 h

4: 83 percent / (i-Pr)2NEt / propan-2-ol / 3.5 h

5: aq. LiOH / 1,2-dimethoxy-ethane / 0.5 h

6: imidazole / 1,2-dimethoxy-ethane / 20 h / 0 - 20 °C

With 1H-imidazole; lithium hydroxide; sodium hydroxide; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; 1,2-dimethoxyethane; water; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/jm00047a001

upstream raw materials:

tert-butyldimethylsilyl chloride

(S)-3-tert-Butylcarbamoyl-4-((2S,4R)-4-carboxy-2-hydroxy-5-phenyl-pentyl)-piperazine-1-carboxylic acid tert-butyl ester

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

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

Downstream raw materials:

indinavir

[14C]-N-Dealkyl Indinavir

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