{(S)-4-[(R)-2-((S)-1-Benzyloxycarbamoyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-phenyl-pentanoylamino]-4-methylcarbamoyl-butyl}-carbamic acid tert-butyl ester

Base Information

• Chemical Name: {(S)-4-[(R)-2-((S)-1-Benzyloxycarbamoyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-phenyl-pentanoylamino]-4-methylcarbamoyl-butyl}-carbamic acid tert-butyl ester
• CAS No.: 679437-31-1
• Molecular Formula: C₃₂H₄₃F₃N₄O₇
• Molecular Weight: 652.711

Synonyms:{(S)-4-[(R)-2-((S)-1-Benzyloxycarbamoyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-phenyl-pentanoylamino]-4-methylcarbamoyl-butyl}-carbamic acid tert-butyl ester

Chemical Property of {(S)-4-[(R)-2-((S)-1-Benzyloxycarbamoyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-phenyl-pentanoylamino]-4-methylcarbamoyl-butyl}-carbamic acid tert-butyl ester

Chemical Property:

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Technology Process of {(S)-4-[(R)-2-((S)-1-Benzyloxycarbamoyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-phenyl-pentanoylamino]-4-methylcarbamoyl-butyl}-carbamic acid tert-butyl ester

There total 6 articles about {(S)-4-[(R)-2-((S)-1-Benzyloxycarbamoyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-phenyl-pentanoylamino]-4-methylcarbamoyl-butyl}-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: 32.0%

N-benzyloxyamine (622-33-3) + (2S,3R)-3-((S)-4-tert-Butoxycarbonylamino-1-methylcarbamoyl-butylcarbamoyl)-2-hydroxy-6-phenyl-2-trifluoromethyl-hexanoic acid (679437-28-6) → {(S)-4-[(R)-2-((S)-1-Benzyloxycarbamoyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-phenyl-pentanoylamino]-4-methylcarbamoyl-butyl}-carbamic acid tert-butyl ester (679437-31-1)

Guidance literature:

(2S,3R)-3-((S)-4-tert-Butoxycarbonylamino-1-methylcarbamoyl-butylcarbamoyl)-2-hydroxy-6-phenyl-2-trifluoromethyl-hexanoic acid; With diethyl phosphorobromidate; thymidine 5'-phosphate; In dichloromethane; N,N-dimethyl-formamide; at 0 ℃; for 0.75h;

N-benzyloxyamine; With thymidine 5'-phosphate; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1016/j.tet.2006.08.036

Reference yield:

N-δ-tert-butoxycarbonyl-L-ornithine methyl amide (178932-85-9) → {(S)-4-[(R)-2-((S)-1-Benzyloxycarbamoyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-phenyl-pentanoylamino]-4-methylcarbamoyl-butyl}-carbamic acid tert-butyl ester (679437-31-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 68 percent / HOAt; HATU; TMP / dimethylformamide / 2 h

2.1: KOH / methanol; H₂O / 2 h

3.1: BrPO(OEt)2; TMP / CH₂Cl₂; dimethylformamide / 0.75 h / 0 °C

3.2: 32 percent / TMP / CH₂Cl₂; dimethylformamide / 0 - 20 °C

With potassium hydroxide; 1-hydroxy-7-aza-benzotriazole; diethyl phosphorobromidate; thymidine 5'-phosphate; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2006.08.036

Reference yield:

1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-5-phenyl-pentan-1-one → {(S)-4-[(R)-2-((S)-1-Benzyloxycarbamoyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-phenyl-pentanoylamino]-4-methylcarbamoyl-butyl}-carbamic acid tert-butyl ester (679437-31-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: TiCl₄; DIPEA / CH₂Cl₂; toluene / 0.33 h / 0 °C

1.2: 59 mg / CH₂Cl₂; toluene / -70 - 20 °C

2.1: 71 percent / potassium carbonate / dioxane; H₂O / 10 h

3.1: 68 percent / HOAt; HATU; TMP / dimethylformamide / 2 h

4.1: KOH / methanol; H₂O / 2 h

5.1: BrPO(OEt)2; TMP / CH₂Cl₂; dimethylformamide / 0.75 h / 0 °C

5.2: 32 percent / TMP / CH₂Cl₂; dimethylformamide / 0 - 20 °C

With potassium hydroxide; 1-hydroxy-7-aza-benzotriazole; diethyl phosphorobromidate; titanium tetrachloride; potassium carbonate; thymidine 5'-phosphate; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tet.2006.08.036

upstream raw materials:

N-benzyloxyamine

(2S,3R)-3-((S)-4-tert-Butoxycarbonylamino-1-methylcarbamoyl-butylcarbamoyl)-2-hydroxy-6-phenyl-2-trifluoromethyl-hexanoic acid

N-δ-tert-butoxycarbonyl-L-ornithine methyl amide

(2S,3R)-2-Hydroxy-3-(3-phenyl-propyl)-2-trifluoromethyl-succinic acid 1-ethyl ester

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