(3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid

Base Information

Chemical Name:(3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid
CAS No.:178267-25-9
Molecular Formula:C₂₂H₃₇NO₅Si
Molecular Weight:423.625
Hs Code.:

Synonyms:(3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid

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Chemical Property of (3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid

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Technology Process of (3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid

There total 10 articles about (3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-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: 92.0%

: 936226-69-6
(3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid ethyl ester

: 178267-25-9
(3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid

Guidance literature:: With sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 4h;
DOI:10.1246/cl.1999.703

Reference yield:

: 1161-13-3
N-Cbz-L-Phe

: 178267-25-9
(3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid

Guidance literature:: Multi-step reaction with 7 steps

1: pTSA

2: 96 percent / toluene / 3 h / Heating

3: 98 percent / H₂; trifluoroacetic acid / Pd/C / methanol / 2 h / 20 °C

4: 92 percent / Et₃N / methanol / 8 h / 20 °C

5: NaBH₄ / methanol / 1 h / 0 - 20 °C

6: 95 percent / imid / dimethylformamide / 10 h / 20 °C

7: 92 percent / NaOH / tetrahydrofuran / 4 h / 20 °C

With 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; hydrogen; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene; 1: Condensation / 2: Alkylation / 3: Hydrogenolysis / 4: Acylation / 5: Reduction / 6: silylation / 7: Hydrolysis;
DOI:10.1246/cl.1999.703

Reference yield:

: 55740-07-3
(4S)-4-benzyl-5-oxo-1,3-oxazolidine-3-carboxylic acid benzyl ester

: 178267-25-9
(3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 96 percent / toluene / 3 h / Heating

2: 98 percent / H₂; trifluoroacetic acid / Pd/C / methanol / 2 h / 20 °C

3: 92 percent / Et₃N / methanol / 8 h / 20 °C

4: NaBH₄ / methanol / 1 h / 0 - 20 °C

5: 95 percent / imid / dimethylformamide / 10 h / 20 °C

6: 92 percent / NaOH / tetrahydrofuran / 4 h / 20 °C

With 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; hydrogen; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene; 1: Alkylation / 2: Hydrogenolysis / 3: Acylation / 4: Reduction / 5: silylation / 6: Hydrolysis;
DOI:10.1246/cl.1999.703