(1R,2'R,1''R,3''S)-acetic acid 1-{4'-[1''-benzyl-4''-(tert-butyldiphenylsilanyloxy)-3''-methylbutylcarbamoyl]thiazol-2'-yl}-3-benzyloxycarbonylamino-4-methylpentyl ester

Base Information

• Chemical Name: (1R,2'R,1''R,3''S)-acetic acid 1-{4'-[1''-benzyl-4''-(tert-butyldiphenylsilanyloxy)-3''-methylbutylcarbamoyl]thiazol-2'-yl}-3-benzyloxycarbonylamino-4-methylpentyl ester
• CAS No.: 796039-52-6
• Molecular Formula: C₄₈H₅₉N₃O₆SSi
• Molecular Weight: 834.164
• Mol file: 796039-52-6.mol

Synonyms:(1R,2'R,1''R,3''S)-acetic acid 1-{4'-[1''-benzyl-4''-(tert-butyldiphenylsilanyloxy)-3''-methylbutylcarbamoyl]thiazol-2'-yl}-3-benzyloxycarbonylamino-4-methylpentyl ester

Chemical Property of (1R,2'R,1''R,3''S)-acetic acid 1-{4'-[1''-benzyl-4''-(tert-butyldiphenylsilanyloxy)-3''-methylbutylcarbamoyl]thiazol-2'-yl}-3-benzyloxycarbonylamino-4-methylpentyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2'R,1''R,3''S)-acetic acid 1-{4'-[1''-benzyl-4''-(tert-butyldiphenylsilanyloxy)-3''-methylbutylcarbamoyl]thiazol-2'-yl}-3-benzyloxycarbonylamino-4-methylpentyl ester

There total 20 articles about (1R,2'R,1''R,3''S)-acetic acid 1-{4'-[1''-benzyl-4''-(tert-butyldiphenylsilanyloxy)-3''-methylbutylcarbamoyl]thiazol-2'-yl}-3-benzyloxycarbonylamino-4-methylpentyl 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: 96.0%

acetic anhydride (108-24-7) + (1R,2'R,1'''R,3'''S)-[1-(2'-{4''-[1'''-benzyl-4'''-(tert-butyldiphenylsilanyloxy)-3'''-methylbutylcarbamoyl]thiazol-2''-yl}-2'-hydroxyethyl)-2-methylpropyl]carbamic acid benzyl ester (796039-51-5) → (1R,2'R,1''R,3''S)-acetic acid 1-{4'-[1''-benzyl-4''-(tert-butyldiphenylsilanyloxy)-3''-methylbutylcarbamoyl]thiazol-2'-yl}-3-benzyloxycarbonylamino-4-methylpentyl ester (796039-52-6)

Guidance literature:

With pyridine; at 20 ℃; for 16h;

DOI:10.1021/ol048252i

Reference yield:

Boc-L-phenylalaninal (72155-45-4) → (1R,2'R,1''R,3''S)-acetic acid 1-{4'-[1''-benzyl-4''-(tert-butyldiphenylsilanyloxy)-3''-methylbutylcarbamoyl]thiazol-2'-yl}-3-benzyloxycarbonylamino-4-methylpentyl ester (796039-52-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 0.25 g / CH₂Cl₂ / 14 h / 0 - 20 °C

2: aq. NaOH / ethanol / 12 h / 20 °C

3: H₂ / Pd/C / methanol / 16 h / 20 °C

4: Et₃N / tetrahydrofuran / 1 h / -40 °C

5: 0.80 g / NaBH₄ / tetrahydrofuran; H₂O / 1 h / 0 - 20 °C

6: 100 percent / imidazole / dimethylformamide / 36 h / 20 °C

7: 72 percent / thioanisole; CF₃COOH / CH₂Cl₂ / 4.5 h / 0 - 20 °C

8: 76 percent / i-Pr₂NEt; DEPBT / dimethylformamide / 14 h / 0 - 20 °C

9: 96 percent / pyridine / 16 h / 20 °C

With pyridine; 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; methyl-phenyl-thioether; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 1: Wiitig olefination;

DOI:10.1021/ol048252i

Reference yield:

(S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol (66605-57-0) → (1R,2'R,1''R,3''S)-acetic acid 1-{4'-[1''-benzyl-4''-(tert-butyldiphenylsilanyloxy)-3''-methylbutylcarbamoyl]thiazol-2'-yl}-3-benzyloxycarbonylamino-4-methylpentyl ester (796039-52-6)

Guidance literature:

Multi-step reaction with 10 steps

1: NaBr; TEMPO; NaOCl / H₂O; toluene; ethyl acetate / 4 h / 0 °C

2: 0.25 g / CH₂Cl₂ / 14 h / 0 - 20 °C

3: aq. NaOH / ethanol / 12 h / 20 °C

4: H₂ / Pd/C / methanol / 16 h / 20 °C

5: Et₃N / tetrahydrofuran / 1 h / -40 °C

6: 0.80 g / NaBH₄ / tetrahydrofuran; H₂O / 1 h / 0 - 20 °C

7: 100 percent / imidazole / dimethylformamide / 36 h / 20 °C

8: 72 percent / thioanisole; CF₃COOH / CH₂Cl₂ / 4.5 h / 0 - 20 °C

9: 76 percent / i-Pr₂NEt; DEPBT / dimethylformamide / 14 h / 0 - 20 °C

10: 96 percent / pyridine / 16 h / 20 °C

With pyridine; 1H-imidazole; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hydroxide; sodium hypochlorite; sodium tetrahydroborate; methyl-phenyl-thioether; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; sodium bromide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; 2: Wiitig olefination;

DOI:10.1021/ol048252i

upstream raw materials:

acetic anhydride

(1R,2'R,1'''R,3'''S)-[1-(2'-{4''-[1'''-benzyl-4'''-(tert-butyldiphenylsilanyloxy)-3'''-methylbutylcarbamoyl]thiazol-2''-yl}-2'-hydroxyethyl)-2-methylpropyl]carbamic acid benzyl ester

Boc-L-phenylalaninal

(S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol

Downstream raw materials:

(1R,3R,1''R,3''S)-acetic acid 1-[4'-(1''-benzyl-4''-hydroxy-3''-methylbutylcarbamoyl)thiazol-2'-yl]-3-benzyloxycarbonylamino-4-methylpentyl ester